37:
1421:. Among its many other effects, the drug caused these cells to decrease their levels of 20-HETE in vitro; the addition of 20-HETE to these cultures rescued the cells from apoptosis. Isoliquiritigenin also inhibits the in vivo lung metastasis of MDA-MB-231 cell transplants while concurrently decreasing the tumor's levels of 20-HETE. The growth of MDA-MB-231 cells implanted into athymic nude female mice as well as the cells' production of a large variety of agents stimulating vascularization including vascular endothelial growth factor were inhibited by treating the mice with an inhibitor of 20-HETE production.
1177:(Cyp4a14(-/-) mice develop male-specific, androgen-dependent hypertension. This seemingly paradoxical result is due to the overexpression of Cyp4a12a; the knockout of Cyp4a14 (Cyp4a14 does not produce 20-HETE) leads to the overexpression of the 20-HETE-producing cytochrome, Cyp4a149(-/-), and consequent overproduction of 20-HETE. The model involves increased plasma androgens, increased vascular and urinary levels of 20-HETE, relief of hypertension by castration, and hypertension which is driven by excessive fluid reabsorption in the kidney's proximal tubule secondary to the overexpression of
280:
1501:
prostaglandin and thromboxane products. In addition, 20-HETE itself blocks prostaglandin and thromboxane metabolites from interacting with the thromboxane receptor. Both effects, i.e. replacement of prostaglandin and thromboxane production with platelet-inactive products and thromboxane A2 receptor blockade, are responsible for 20-HETE's platelet aggregation-inhibiting action. However, the platelet anti-aggregating activity of 20-HETE requires micromolar levels and therefore may be more of a pharmacological than physiological activity.
1248:=2.31); 1538 males and females from the Framingham Heart Study (Odds ratio=1.23); males but not females in 732 black Americans with hypertensive renal disease participating in the African American Study of Kidney Disease; males in a sample of 507 individuals in Japan and in the third MONICA (MONitoring trends and determinants In Cardiovascular disease survey of 1397 individuals the homozygous C8590C genotype to the homozygous T8590T genotype with odds ratios of 3.31 for all subjects, 4.30 for males 2.93 for women);
1271:(adjusted odds ratio of 1.50 in comparing homozygous and heterozygous C296T subjects to homozygous C286C subjects) in >2000 individuals taken from the Han Chinese population. The effect of the β296C>T single base pair substitution on baseline CYP411 transcriptional activity was not significant, suggesting that this polymorphism may not be the causal variant but instead may be in linkage disequilibrium with the causal variant. Regardless, this SNP may serve as a
1436:-binding sites, including those for miR-211, miR-125a-3p, miR-197, miR-1226, and miR-204'. Since these miRNA's reduce the translation of CYP4Z1, the expression of CYP4Z2P can bind these miRNAs to reduce their interference with CYP4Z1 and thereby increase the production of CYP4Z1 protein and perhaps 20-HETE; indeed, force expression of these 3'UTRs promoted in vitro tumor angiogenesis in breast cancer cells partly via miRNA-dependent activation of the
1001:. While significantly less potent than thromboxane A2 in activating this receptor, studies on rat and human cerebral artery preparations indicate that increased blood flow through these arteries triggers production of 20-HETE which in turn binds to thromboxane receptors to constrict these vessels and thereby reduce their blood blow. Acting in the latter capacity, 20-HETE, it is proposed, functions as a mediator regulating blood flow to the brain.
1517:. While significantly less potent than thromboxane A2 in activating this receptor, studies on human cerebral artery preparations indicate that increased blood flow through these arteries triggers production of 20-HETE which in turn binds to thromboxane receptors to constrict these vessels and thereby reduce their blood blow. Acting in the latter capacity, 20-HETE, it is proposed, functions as a mediator regulating blood flow to the human brain.
838:
activities to their prostaglandin and thromboxane precursors and since the 12-hydroxy and 11-hydroxy metabolites of 20-HETE may also be inactive, these metabolic pathways appear to function in inactivating 20-HETE with respect to the platelet system. However, the 20-hydroxy prostaglandin metabolites are able to contract rat aorta rings and thereby could contribute to the hypertensive actions of 20-HETE.
940:, angiotensin II. 20-HETE has a particularly complex interaction with the renin angiotensin system: angiotensin II stimulates the preglomerular microvessels of the rat kidney to produce 20-HETE; this production is required for angiotensin II to exert its full constrictor effects; and 20-HETE induces transcription of the enzyme which converts angiotensin I to angiotensin II, i.e.
719:, respectively. While many of the effects and diseases associated with the over- or under-expression, pharmacological inhibition, and single nucleotide or mutant variants of the cytochrome Ο-hydroxylases have been attributed to their impact on 20-HETE production, the influence of these alternate metabolic actions have frequently not been defined.
1193:(EETs). The model involves normal levels of 20-HETE, reduced expression of Cyp2c44, reduced levels of EETs, and deficiencies in kidney tubule absorption of sodium regulated by EETs, and the normalization of hypertensive blood pressure by increasing expression of Cyp2c44 by treating the mice with an inducer of its expression, an activator of
1149:
infused kidney, and produced a mean arterial pressure rise from 115 at baseline to 142 mm of mercury; this study indicates that the hypertensive versus hypotensive effects of 20-HETE depend not only on the organ of its production but also, with respect to the kidney, the site within the organ where it is produced.
1312:(i.e. ischemic stroke) in a study of 175 subjects with infarction compared to 246 control subjects in Japan, in 507 stroke patients compared to 487 age- and sex-matched 487 controls in India, and in males but not females in a study of 558 patients compared to 557 controls in China. The variant is associated with
890:
this organ and species. Coronary artery endothelial cells isolated from pigs incorporate 20-HETE primarily into the sn-2 position of phospholipids through a coenzyme A-dependent process. It is likely, although not yet shown, that these mouse and pig 20-HETE metabolizing pathways also occur in humans.
1148:
models) that had one kidney removed and then fed a high salt diet are hypertensive. Kidney medullary interstitial infusion of an inhibitor of 20-HETE production reduced the formation of 20-HETE in the outer medulla of the infused kidney, had no effect on the production of 20-HETE in the cortex of the
1103:
As indicated above, 20-HETE may raise blood pressure by constricting arterial blood vessels but also may lower blood pressure by promoting the loss of sodium and fluids in the kidneys. The effects of 20-HETE therefore are complex, as indicated in studies of the following animal models. Many of these
1486:
glioma cells in culture; since these cells could not be shown to produce 20-HETE, it was proposed that some other metabolite may by the inhibitor's targeted cytochrome enzymes was responsible for maintaining these cells growth. It is also possible that any such inhibitor has off-target effects that
480:
reaction. CYP450 enzymes belong to a superfamily which in humans is composed of at least 57 members and in mice at least 120 members. Among this superfamily, certain members of the CYP4A and CYP4F subfamilies in the CYP4 family are considered predominant cytochrome P450 enzymes that are responsible
1444:
and thereby stimulating the production of vascular endothelium growth factor and possibly other endothelium growth factors. Taken together, these pre-clinical studies suggest that 20-HETE made by one or more of the cited cytochrome P450 enzymes may contribute to the progression of breast cancer by
1227:
Human CYP4A11 has 72.69% amino acid identity with murine cyp4a14 and 73.02% identity with murine cyp4a10 suggesting that it plays a role in humans similar to that of cyp4a14 and/or cyp4a10 in mice. The association of hypertension with defective CYP4A11 in humans as indicated below seems to parallel
898:
20-HETE-synthesizing enzymes are widely distributed to liver, kidney, brain, lung, intestine and blood vessels. In most vascular systems, 20-HETE synthesizing activity is limited to vascular smooth muscle of small blood vessels with little or no such activity in the vessel's endothelial cells or in
1500:
to mediate and/or promote the ensuing platelet aggregation response to most stimuli. The platelets metabolize 20-HETE to the 20-hydroxy analogs of prostaglandin H2 and thromboxane A2, products that are essentially inactive in platelets, while consequently form less of the arachidonic acid-derived
1316:
in a study of 507 patients compared to 487 age- and sex-matched controls in India, in males but not females in a study of 234 patients compared to 248 control subjects in Japan, and in male but not female patients in Sweden enrolled in the cardiovascular cohort of the Malmo Diet and Cancer Study.
889:
reactions. These shortening pathways also are likely to serve in inactivating 20-HETE, although the initial product of this shortening pathway, 20-carboxy-HETE, dilates coronary microvessels in the pig heart and thereby could serve to antagonize the vasoconstrictor actions of 20-HETE, at least in
666:
inhibitors may act as perhaps unwanted side effects to increase the levels of 20-HETE. There are a variety of pharmacological agents which inhibit the synthesis of 20-HETE including various fatty acid analogs that compete reversibly with arachidonic acid for the substrate binding site in the CYP
543:
with the predominant 20-HETE-synthesizing enzymes being CYP4F2, which is the major 20-HETE producing enzyme in the human kidney, followed by CYP4A11. CYP4F3 is expressed as two distinct enzymes, CYP4F3A and CYP4F3B, due to alternative splicing of a single pre-mRNA precursor molecule; CYP4F3A is
1367:
dysfunction. A second homozygous enzyme-disabling mutation has been identified in CYP2U1, c.1A>C/p.Met1?, that is associated with <1% of hereditary spastic paraplegia sufferers. While the role of 20-HETE in these mutations has not been established, the reduction in 20-HETE production and
837:
of the hydroperoxy and hydroxyl residues at positions 11 and 12 in the eicosatetraenoic acids are predicted based on studies defining the chirality of the arachidonic metabolites made by these enzymes.) Since the prostaglandin and thromboxane metabolites of 20-HETE lack the platelet-stimulating
438:
including the regulation of vascular tone, blood flow to specific organs, sodium and fluid transport in the kidney, and vascular pathway remodeling. These vascular and kidney effects of 20-HETE have been shown to be responsible for regulating blood pressure and blood flow to specific organs in
1481:
While these studies suggest that CYP4A11, CYP4A22, CYP4F2, and/or CYP4F3 produce 20-HETE which in turn promotes the growth of the cited cancers in model systems and therefore may do so in the human cancers, this suggestion clearly needs much further study. For example, an inhibitor of 20-HETE
1304:
in comparing 249 patients with hypertension to 238 age-matched controls in Japan, the variant was not associated with hypertension. The maintenance of the lower blood pressure that followed diet-induced weight loss was more difficult for carriers of the Val433Met variant and may be related to
1251:
A study of 1501 participants recruited from the Tanno-Sobetsu Study found that the variant -845G in the promoter region of CYP411 (β845A is the predominant genotype) is associated with reduced transcription of CYP411 as well as with hypertension (odds ratio of homozygous and heterozygous -845G
1024:
rats that underwent balloon injury of the common carotid artery exhibited elevated levels of CYP4A enzyme immunostaining in the smooth muscle of the injured arteries as well as elevated levels of 20-HETE in the injured arteries. Inhibition of 20-HETE production by two different agents greatly
1477:
Messenger RNAs for CYP4A11, CYP4A22, CYP4F2, and/or CYP4F3 are more highly expressed in ovary, colon, thyroid, lung, ovary, cancers compared to their normal tissue counterparts; in ovarian cancer, this higher expression is associated with an increased level of CYP4F2 protein expression and an
1104:
models appear relevant to hypertension in humans in that they parallel the human disease, i.e. men have higher rates of hypertension than women, and women with increased levels of androgens (e.g. postmenopausal women and women with polycystic ovarian disease) and higher rates of hypertension.
568:
In mice, the only 20-HETE- and 19-HETE-producing enzymes of the Cyp4a subfamily are two extensively homologous ones, Cyp4a12a and Cyp4a12b; Cyp4a12a is expressed in the male kidney in an androgen hormone-dependent manner. In rats, Cyp4a1, Cyp4a2, Cyp4a3, and Cyp4a8 make 20-HETE. The tissue
556:, the only member of the human CYP2U subfamily, is highly expressed in brain and thymus and to lesser extents in numerous other tissues such as kidney, lung and heart. CYP2U1 protein is also highly expressed, compared to several other cytochrome P450 enzymes, in malignant breast tissue; the
1184:
Mice depleted of Cyp4a10 maintain normal blood pressure on a low salt diet but become hypertensive on normal or high salt diets; this paradoxical result appears due to a decrease in kidney levels of Cyp2C44 caused by the loss of Cyp4a10. Cyp2C44 metabolizes arachidonic acid a family of
1239:
rs1126742 variant of CYP4A11 switches thymidine to cytosine at nucleotide 8590 and leads to a phenylalanine-to-serine substitution at amino acid 434); this F434S variant has significantly reduced ability to Ο-oxidize arachidonic acid to 20-HETE and has been associated with
1136:
that in turn stimulates the CYp4A/20-HETE pathway. Non-selective and non-selective inhibitors of CYP4A and 20-HETE production reduce hypertension in this model. The hypertension in this model is more severe in male rats and appears to be mediated at least in part by
1283:
The T allele at rs2108622, which has been designated as CYP4F2*3 in the Human CYP Allele
Nomenclature Database by the Pharmacogene Variation Consortium, produces the CYP4F2 enzyme with methionine residue instead of valine at position 433 (the Val433Met variant), a
1004:
These vasoconstrictor effects of 20-HETE can reduce blood flow to specific parts of the body, not only to brain (see previous paragraph) but also to kidney, liver, heart and other organs, as well as to portions of these organs; they can also contribute to systemic
1461:
cell line U251 and, when forced to overexpress CYP4Z1 by gene transfection, overproduced 20-HETE and exhibited a dramatically increased rate of growth that was blocked by inhibiting the cells from producing 20-HETE. A similar set of findings was found with human
1029:
hyperplasia and vascular remodeling that occurred after balloon injury. The studies suggest that the increase in expression of CYP4A and production of 20-HETE contribute to vascular intima growth, remolding, and thereby healing of injured rat carotid arteries.
986:; this inhibits the ability of eNOS to become activated. The endothelial cells become dysfunctional in exhibiting decreased ability to produce the vasodilating agent, nitric oxide, and in containing elevated levels of a potentially injurious oxygen radical,
443:; genetic and preclinical studies suggest that 20-HETE may similarly regulate blood pressure and contribute to the development of stroke and heart attacks. Additionally the loss of its production appears to be one cause of the human neurological disease,
2194:
Thomas RD, Green MR, Wilson C, Weckle AL, Duanmu Z, Kocarek TA, et al. (2006). "Cytochrome P450 expression and metabolic activation of cooked food mutagen 2-amino-1-methyl-6-phenylimidazo4,5-bpyridine (PhIP) in MCF10A breast epithelial cells".
4977:
Tatarunas V, Jankauskiene L, Kupstyte N, Skipskis V, Gustiene O, Grybauskas P, et al. (2014). "The role of clinical parameters and of CYP2C19 G681 and CYP4F2 G1347A polymorphisms on platelet reactivity during dual antiplatelet therapy".
1495:
20-HETE inhibits the aggregation of human platelets by competing with arachidonic acid for the enzymes that produce prostaglandin H2 and thromboxane A2. These products are formed in response to platelet stimulation and then act through the
5206:
Li Y, Zhao H, Wang Y, Zheng H, Yu W, Chai H, et al. (2013). "Isoliquiritigenin induces growth inhibition and apoptosis through downregulating arachidonic acid metabolic network and the deactivation of PI3K/Akt in human breast cancer".
5021:
Kim WY, Lee SJ, Min J, Oh KS, Kim DH, Kim HS, et al. (2018). "Identification of novel CYP4F2 genetic variants exhibiting decreased catalytic activity in the conversion of arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE)".
5253:
Zheng H, Li Y, Wang Y, Zhao H, Zhang J, Chai H, et al. (2014). "Downregulation of COX-2 and CYP 4A signaling by isoliquiritigenin inhibits human breast cancer metastasis through preventing anoikis resistance, migration and invasion".
1288:(1347C>T; NM_001082.5:c.1297G>A; p. Val433Met; rs2108622). This variant of the CYP4F2 enzyme has reduced capacity to metabolize arachidonic acid to 20-HETE but increased urinary excretion of 20-HETE. Studies found that:
1169:
mice overexpressing Cyp4a12 develop androgen-independent hypertension that is associated with increased levels of 20-HETE; this hypertension is fully reversible by treatment with a Cyp4a selective inhibitor of 20-HETE production.
707:, vascular responses, and other reactions. This metabolism-induced inactivation may underlie the proposed roles of the cytochromes in dampening inflammatory responses and the reported associations of certain CYP4F2 and CYP4F3
3169:
Watzer B, Reinalter S, Seyberth HW, Schweer H (2000). "Determination of free and glucuronide conjugated 20-hydroxyarachidonic acid (20-HETE) in urine by gas chromatography/negative ion chemical ionization mass spectrometry".
1115:
exhibit elevated levels of CYP4A2 and 20-HETE; blockade of 20-HETE production lowers blood pressure in this model. The effect is particularly well seen in female rats: aging post-menopausal but not pre-menopausal female
3246:
Hill E, Murphy RC (May 1992). "Quantitation of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) produced by human polymorphonuclear leukocytes using electron capture ionization gas chromatography/mass spectrometry".
1868:"CYP4 enzymes as potential drug targets: Focus on enzyme multiplicity, inducers and inhibitors, and therapeutic modulation of 20-hydroxyeicosatetraenoic acid (20-HETE) synthase and fatty acid Ο-hydroxylase activities"
7535:
6671:
6406:
2674:
Kikuta Y, Kusunose E, Sumimoto H, Mizukami Y, Takeshige K, Sakaki T, et al. (1998). "Purification and characterization of recombinant human neutrophil leukotriene B4 omega-hydroxylase (cytochrome P450 4F3)".
1317:
The incidence of cerebral and myocardial infarction in these studies appears to be independent of hypertension. (The platelets of individuals heterozygous or homozygous for the Val433Met variant exhibit increased
520:)-HETE, inhibits the action of 20-HETE on vascular endothelial cells. Based on studies analyzing the production of other HETEs by CYP enzymes, the production of 19-HETE by these enzymes may include both its
3358:
Zhang F, Wang MH, Wang JS, Zand B, Gopal VR, Falck JR, et al. (2004). "Transfection of CYP4A1 cDNA decreases diameter and increases responsiveness of gracilis muscle arterioles to constrictor stimuli".
1066:
which in turn stimulates the adhesion of platelets to the endothelial cells. The endothelial, platelet, and pro-clotting actions of 20-HETE may contribute to its ability to disrupt blood flood to tissues.
2112:
Toselli F, Booth Depaz IM, Worrall S, Etheridge N, Dodd PR, Wilce PA, et al. (2015). "Expression of CYP2E1 and CYP2U1 proteins in amygdala and prefrontal cortex: Influence of alcoholism and smoking".
5152:
Citterio A, Arnoldi A, Panzeri E, d'Angelo MG, Filosto M, Dilena R, et al. (2014). "Mutations in CYP2U1, DDHD2 and GBA2 genes are rare causes of complicated forms of hereditary spastic paraparesis".
3000:"Different catalytically competent arrangements of arachidonic acid within the cyclooxygenase active site of prostaglandin endoperoxide H synthase-1 lead to the formation of different oxygenated products"
5732:
Guo M, Roman RJ, Falck JR, Edwards PA, Scicli AG (2005). "Human U251 glioma cell proliferation is suppressed by HET0016 N-hydroxy-N'-(4-butyl-2-methylphenyl)formamidine, a selective inhibitor of CYP4A".
1336:
of CYP4F2 is associated with essential hypertension in men only in a study of 249 hypertensive versus 238 age-matched controls in Japan. The impact of this variant on CYP4F2 expression is not known.
5828:
5689:
Rieger MA, Ebner R, Bell DR, Kiessling A, Rohayem J, Schmitz M, et al. (2004). "Identification of a novel mammary-restricted cytochrome P450, CYP4Z1, with overexpression in breast carcinoma".
1296:
among a large number of
Swedish patients enrolled and monitored over 10 years in the cardiovascular cohort of the MalmΓΆ Diet and Cancer Study only males with this variant exhibited hypertension;
4877:
1424:
Messenger RNAs not only for CYP4Z2 but also for CYP4A11, CYP4A22, CYP4F2, and CYP4F3 are more highly expressed in samples of human breast cancer tumors compared to normal breast tissue. The
1363:
as well as other cytochrome P450 proteins; the p.Asp314Val mutation is located in the enzyme's functional domain, is predicted to be damaging to the enzyme's activity, and is associated with
3282:
Tsai IJ, Croft KD, Puddey IB, Beilin LJ, Barden A (Apr 2011). "20-Hydroxyeicosatetraenoic acid synthesis is increased in human neutrophils and platelets by angiotensin II and endothelin-1".
5646:
Downie D, McFadyen MC, Rooney PH, Cruickshank ME, Parkin DE, Miller ID, et al. (2005). "Profiling cytochrome P450 expression in ovarian cancer: Identification of prognostic markers".
2077:
Devos A, Lino
Cardenas CL, Glowacki F, Engels A, Lo-Guidice JM, Chevalier D, et al. (2010). "Genetic polymorphism of CYP2U1, a cytochrome P450 involved in fatty acids hydroxylation".
1132:) and ameliorated by low salt intake. In this model, rats exhibit an up-regulated CYP4A/20-HETE pathway within their cerebral vasculature and vascular endothelial cell overproduction of
576:
Mouse CYP2J9, rat CYP2J3, and sheep CYP2J metabolize arachidonic acid primarily to 19-HETE but also to smaller amounts of 20-HETE, and, in the case of the sheep enzyme, 18-HETE; human
4750:
Munshi A, Sharma V, Kaul S, Al-Hazzani A, Alshatwi AA, Shafi G, et al. (2012). "Association of 1347 G/A cytochrome P450 4F2 (CYP4F2) gene variant with hypertension and stroke".
924:
In various rodent models, 20-HETE, at low concentrations (<50 nanomolar), acts to constrict arteries by sensitizing (i.e. increasing) the contraction responses of these artery's
7296:
1478:
increased ability to metabolize arachidonic acid to 20-HETE. Ovarian cancers also overexpress CYP4Z1 mRNA protein; this overexpression is associated with a poorer disease outcome.
3126:
Ward NC, Rivera J, Hodgson J, Puddey IB, Beilin LJ, Falck JR, et al. (2004). "Urinary 20-hydroxyeicosatetraenoic acid is associated with endothelial dysfunction in humans".
1325:. This platelet hyper-responsiveness to epinephrine, particularly if also exhibited to other platelet-aggregating agents, could contribute to cerebral and coronary infarctions.)
3394:
Kaide J, Zhang F, Wei Y, Wang W, Gopal VR, Falck JR, et al. (2004). "Vascular CO counterbalances the sensitizing influence of 20-HETE on agonist-induced vasoconstriction".
1181:; these effects are presumed but not yet shown to be due to the overproduction of 20-HETE. The Cyp4a12-transgenic model (above) is referred to in support of this presumption.
1758:
Bylund J, Ericsson J, Oliw EH (1998). "Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS".
675:
The cytochrome Ο-oxidases including those belonging to the CYP4A and CYP4F sub-families and CYPU21 hydroxylate not only arachidonic acid but also various shorter chain (e.g.
6060:
5821:
4258:
Imaoka S, Ogawa H, Kimura S, Gonzalez FJ (1993). "Complete cDNA sequence and cDNA-directed expression of CYP4A11, a fatty acid omega-hydroxylase expressed in human kidney".
1529:
exhibited significantly elevated levels of plasma and urinary 20-HETE compared to matched controls; women with the syndrome had particularly higher urinary 20-HETE levels.
1157:
Androgen treatment causes hypertension in normal male and female rats; this hypertensive response is greatly reduced by diverse inhibitors of Cyp4a and 20-HETE production.
1359:
in that it segregates with the disease at the homozygous state in two afflicted families. The mutation affects an amino acid (p.Asp316Val) highly conserved among CYP2U1
5776:
Tsai IJ, Croft KD, Mori TA, Falck JR, Beilin LJ, Puddey IB, et al. (2009). "20-HETE and F2-isoprostanes in the metabolic syndrome: The effect of weight reduction".
5109:
Wortmann SB, Espeel M, Almeida L, Reimer A, Bosboom D, Roels F, et al. (2015). "Inborn errors of metabolism in the biosynthesis and remodelling of phospholipids".
4413:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008). "A haplotype of the CYP4A11 gene associated with essential hypertension in
Japanese men".
4942:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2009). "A haplotype of the CYP4F2 gene associated with myocardial infarction in
Japanese men".
447:. Preclinical studies also suggest that the overproduction of 20-HETE may contribute to the progression of certain human cancers, particularly those of the breast.
5814:
1405:
mice show a greater increase in tumor weight and vascularity compared to control T47D cells; these increases are prevented by an inhibitor of 20-HETE production.
1292:
among 161 hypertensive and 74 normotensive subjects in
Australia, the incidence of the Val433Met variant was significantly increased in the hypertensive subjects;
1974:
Corcos L, Lucas D, Le Jossic-Corcos C, DrΓ©ano Y, Simon B, PlΓ©e-Gautier E, et al. (2012). "Human cytochrome P450 4F3: Structure, functions, and prospects".
3439:"Dietary Omega-3 Polyunsaturated Fatty Acids Prevent Vascular Dysfunction and Attenuate Cytochrome P4501A1 Expression by 2,3,7,8-Tetrachlorodibenzo-P-Dioxin"
906:
and platelets and by the ascending tubule cells in the medulla as well the pre-glomerular arterioles and certain other localized areas of the rabbit kidney.
125:
5418:
Zheng L, Li X, Gu Y, Lv X, Xi T (2015). "The 3'UTR of the pseudogene CYP4Z2P promotes tumor angiogenesis in breast cancer by acting as a ceRNA for CYP4Z1".
7014:
6299:
6033:
3087:"Metabolism of 20-hydroxyeicosatetraenoic acid by cyclooxygenase. Formation and identification of novel endothelium-dependent vasoconstrictor metabolites"
7242:
2557:"Renal drug metabolism in humans: The potential for drug-endobiotic interactions involving cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT)"
310:
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
1209:, also known as the capsaicin receptor and the vanilloid receptor 1), and through this receptor, cultured dorsal root ganglion cells taken from mice.
4839:"The effect of a single nucleotide polymorphism of the CYP4F2 gene on blood pressure and 20-hydroxyeicosatetraenoic acid excretion after weight loss"
4838:
5358:"Gene expression profiling reveals new aspects of PIK3CA mutation in ERalpha-positive breast cancer: Major implication of the Wnt signaling pathway"
5299:"HET0016, a selective inhibitor of 20-HETE synthesis, decreases pro-angiogenic factors and inhibits growth of triple negative breast cancer in mice"
4627:"Hypertension, cardiovascular risk and polymorphisms in genes controlling the cytochrome P450 pathway of arachidonic acid: A sex-specific relation?"
899:
large blood vessels. However, both the smooth muscle and endothelial cells obtained from mouse brain microvasculature, produce 20-HETE in culture.
3643:
Wang J, Li H, He J, Li B, Bao Q, Zhang X, et al. (2015). "20-Hydroxyeicosatetraenoic acid involved in endothelial activation and thrombosis".
3596:"20-Hydroxyeicosatetraenoic acid inhibition attenuates balloon injury-induced neointima formation and vascular remodeling in rat carotid arteries"
6538:
2910:"Omega-oxidation of 20-hydroxyeicosatetraenoic acid (20-HETE) in cerebral microvascular smooth muscle and endothelium by alcohol dehydrogenase 4"
990:; the blood vessels to which these dysfunctional endothelial cells belong are less able to dilate in response to the vasodilator, acetylcholine.
17:
6543:
548:, which is expressed in a limited range of tissues such as human breast and ovary, may also metabolize arachidonic acid to 20-HETE while human
1723:, Narsimhaswamy D, Pritchard Jr KA, et al. (2008). "20-hydroxyeicosatetraenoic acid causes endothelial dysfunction via eNOS uncoupling".
1120:
exhibit highly significant falls in blood pressure when treated with non-selective or selective inhibitors of CYP-induced 20-HETE production.
7625:
7485:
6497:
6426:
2753:"Interactions between the dietary polyunsaturated fatty acid ratio and genetic factors determine susceptibility to pediatric Crohn's disease"
6676:
323:
7480:
7341:
6736:
6635:
6588:
6518:
4115:
Fidelis P, Wilson L, Thomas K, Villalobos M, Oyekan AO (2010). "Renal function and vasomotor activity in mice lacking the Cyp4a14 gene".
7585:
3319:"Structural identification of cytochrome P450-dependent arachidonate metabolites formed by rabbit medullary thick ascending limb cells"
3046:"A single nucleotide polymorphism in the CYP4F2 but not CYP4A11 gene is associated with increased 20-HETE excretion and blood pressure"
3729:"Roles played by 20-HETE, angiotensin II and endothelin in mediating the hypertension in aging female spontaneously hypertensive rats"
1347:(2024C>G P85A; 80 C>T A27V rs771576634; 139C>T R47C rs115517770) which may affect conversion of arachidonic acid to HETE-20.
841:
Cultured smooth muscle and endothelial cells from mouse brain microvasculature oxidize 20-HETE to its 20-carboxy analog, 20-carboxy- 5
7600:
5507:"Cytochrome P450 Ο-hydroxylase promotes angiogenesis and metastasis by upregulation of VEGF and MMP-9 in non-small cell lung cancer"
3825:
Crofton JT, Ota M, Share L (1993). "Role of vasopressin, the renin-angiotensin system and sex in Dahl salt-sensitive hypertension".
224:
6578:
1386:
6817:
6789:
1471:
6456:
2151:
Murray GI, Patimalla S, Stewart KN, Miller ID, Heys SD (2010). "Profiling the expression of cytochrome P450 in breast cancer".
1639:"CYP2U1, a novel human thymus- and brain-specific cytochrome P450, catalyzes omega- and (omega-1)-hydroxylation of fatty acids"
1055:
643:
4662:
6843:
6809:
3547:"Impact of vascular thromboxane prostanoid receptor activation on hemostasis, thrombosis, oxidative stress, and inflammation"
2951:"Downregulation of human platelet reactivity by neutrophils. Participation of lipoxygenase derivatives and adhesive proteins"
1051:
187:
4209:"20-Hydroxyeicosatetraenoic acid (20-HETE) is a novel activator of transient receptor potential vanilloid 1 (TRPV1) channel"
1474:
cell lines in culture; the 20-HETE antagonist also inhibited the growth of 786-O cells transplanted into athymic nude mice.
956:. likewise stimulate 20-HETE production and have vasoconstrictive actions which are enhanced by 20-HETE. These circular or
5837:
1394:
7580:
6696:
6436:
1681:
Hardwick JP (2008). "Cytochrome P450 omega hydroxylase (CYP4) function in fatty acid metabolism and metabolic diseases".
1466:
cells. A selective inhibitor of 20-HETE synthesis and a 20-HETE antagonist reduced the growth of two human kidney cancer
1267:) variant of CYP4A11, C296T (cytosine to thymine at position 296), was associated with a significantly increased risk of
964:
5062:"Alteration of fatty-acid-metabolizing enzymes affects mitochondrial form and function in hereditary spastic paraplegia"
4499:"A polymorphism regulates CYP4A11 transcriptional activity and is associated with hypertension in a Japanese population"
2805:"Determination of major UDP-glucuronosyltransferase enzymes and their genotypes responsible for 20-HETE glucuronidation"
1368:
thereby 20-HETE's activation of the TRPV1 receptor in nerve tissues, it is hypothesized, may contribute to the disease.
4688:"The V433M variant of the CYP4F2 is associated with ischemic stroke in male Swedes beyond its effect on blood pressure"
4590:
Stec DE, Roman RJ, Flasch A, Rieder MJ (2007). "Functional polymorphism in human CYP4F2 decreases 20-HETE production".
4458:"Association of the T8590C polymorphism of CYP4A11 with hypertension in the MONICA Augsburg echocardiographic substudy"
1079:
in the epithelial cells of the proximal tubules of the kidney; the kinase then phosphorylates and thereby inhibits the
5556:"Down-regulation of 20-HETE synthesis and signaling inhibits renal adenocarcinoma cell proliferation and tumor growth"
469:
294:
2639:
Konkel A, Schunck WH (2011). "Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids".
552:, once considered as contributing to 20-HETE production, is now regarded as being metabolically inactive. Finally,
1178:
683:) fatty acids. They can also Ο-hydroxylate and thereby reduce the activity of various fatty acid metabolites (e.g.
4295:"Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension"
2604:
Kroetz DL, Xu F (2005). "Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation".
2247:"Arachidonic acid monooxygenase: Genetic and biochemical approaches to physiological/pathophysiological relevance"
1550:
Kroetz DL, Xu F (2005). "Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation".
395:
7658:
1425:
1128:
Dahl salt-sensitive rats develop hypertension that develops more quickly and exacerbated by high intake of salt (
1088:
4160:"Salt-sensitive hypertension is associated with dysfunctional Cyp4a10 gene and kidney epithelial sodium channel"
3870:"Testosterone-dependent hypertension and upregulation of intrarenal angiotensinogen in Dahl salt-sensitive rats"
7545:
6966:
6961:
6411:
1340:
1329:
1285:
1260:
1117:
1112:
2782:
6946:
6941:
5888:
4798:"Haplotype-based case-control study of the human CYP4F2 gene and essential hypertension in Japanese subjects"
1356:
941:
444:
7654:
6931:
6492:
4068:"Increased renal proximal convoluted tubule transport contributes to hypertension in Cyp4a14 knockout mice"
3493:"Isolated human and rat cerebral arteries constrict to increases in flow: role of 20-HETE and TP receptors"
974:
Studies in rats also indicate that in vascular endothelial cells 20-HETE inhibits the association of the
731:
692:
639:
258:
1205:
20-HETE activates the mouse and human transient receptor potential cation channel subfamily V member 1 (
36:
1463:
1437:
1010:
734:(UGTs) is thought to be a primary pathway of 20-HETE elimination and thereby inactivation in humans.
708:
570:
275:
4704:
4311:
7046:
6956:
6951:
6936:
6753:
6253:
5883:
5878:
1401:-2. T47D cells that overexpress CYP4Z1 also overproduce 20-HETE and when transplanted into athymic
1190:
1050:-inducing agent, ferric chloride, in the common carotid and femoral arteries; companion studies on
937:
218:
638:
binding site of the 20-HETE producing cytochrome p450 enzymes. Drugs that are substrates for the
7237:
7019:
5597:"Targeting 20-HETE producing enzymes in cancer - rationale, pharmacology, and clinical potential"
5297:
Borin TF, Zuccari DA, Jardim-Perassi BV, Ferreira LC, Iskander AS, Varma NR, et al. (2014).
1133:
873:-octadecatetraenoic acid, and then to the further chain-shortened dicarboxylic acid, 16-carboxy-5
4543:"Association of common variants of CYP4A11 and CYP4F2 with stroke in the Han Chinese population"
600:
are particularly potent stimulators of this production. Other stimulators include the powerful
7540:
7387:
7104:
6976:
6882:
6248:
5893:
4699:
4306:
3960:"Androgen-sensitive hypertension associates with upregulated vascular CYP4A12-20-HETE synthase"
3868:
Yanes LL, Sartori-Valinotti JC, Iliescu R, Romero DG, Racusen LC, Zhang H, et al. (2009).
1241:
1059:
968:
4399:
4009:"Alterations in the regulation of androgen-sensitive Cyp 4a monooxygenases cause hypertension"
2617:
2022:"Increased expression of CYP4Z1 promotes tumor angiogenesis and growth in human breast cancer"
1563:
7678:
7215:
5356:
Cizkova M, Cizeron-Clairac G, Vacher S, Susini A, Andrieu C, Lidereau R, et al. (2010).
4387:
2856:"Biological activity and metabolism of 20-hydroxyeicosatetraenoic acid in the human platelet"
1313:
1084:
1063:
993:
20-HETE can also constrict rodent (and human) artery preparations by directly activating the
983:
979:
165:
3919:"Inhibition of renal outer medullary 20-HETE production produces hypertension in Lewis rats"
1355:
A mutation (c.947A>T) in CYP2U1 has been associated with a small number of patients with
7688:
7683:
7595:
7416:
7358:
7287:
7195:
7148:
6583:
6446:
6384:
6364:
6238:
5926:
5369:
5310:
5263:
5216:
4020:
2404:"Androgen-induced hypertension in angiotensinogen deficient mice: Role of 20-HETE and EETS"
2204:
2033:
1510:
1497:
1318:
1300:
among several hundred subjects in India, the variant was associated with hypertension; and
994:
680:
101:
49:
4837:
Ward NC, Croft KD, Puddey IB, Phillips M, Van
Bockxmeer F, Beilin LJ, et al. (2014).
3778:"Role of the CYP4A/20-HETE pathway in vascular dysfunction of the Dahl salt-sensitive rat"
279:
8:
7500:
7420:
7362:
7320:
7262:
7030:
6209:
4642:
4344:
Gainer JV, Lipkowitz MS, Yu C, Waterman MR, Dawson EP, Capdevila JH, et al. (2008).
3044:
Ward NC, Tsai IJ, Barden A, Van
Bockxmeer FM, Puddey IB, Hodgson JM, et al. (2008).
2415:
2367:
2262:
1823:
1309:
925:
91:
5789:
5373:
5314:
5267:
5220:
4024:
3205:
Kaduce TL, Fang X, Harmon SD, Oltman CL, Dellsperger KC, Teesch LM, et al. (2004).
2208:
2037:
145:
7381:
7247:
7042:
6988:
6553:
6227:
6119:
5905:
5852:
5758:
5714:
5671:
5623:
5596:
5572:
5555:
5531:
5506:
5482:
5465:
5443:
5392:
5357:
5333:
5298:
5188:
5134:
5086:
5061:
5003:
4903:"A haplotype of the CYP4F2 gene is associated with cerebral infarction in Japanese men"
4869:
4775:
4727:
4714:
4687:
4654:
4603:
4567:
4542:
4515:
4498:
4474:
4457:
4438:
4370:
4345:
4321:
4294:
4235:
4208:
4184:
4159:
4140:
4092:
4067:
3984:
3959:
3894:
3869:
3850:
3802:
3777:
3753:
3728:
3704:
3679:
3620:
3595:
3576:
3517:
3492:
3463:
3438:
3419:
3407:
3151:
3139:
3062:
3045:
2880:
2871:
2855:
2831:
2804:
2581:
2556:
2532:
2507:
2483:
2424:
2403:
2376:
2351:
2320:
2295:
2271:
2246:
2176:
2054:
2021:
1999:
1948:
1923:
1892:
1867:
1832:
1807:
1611:
1586:
1526:
1446:
712:
4497:
Sugimoto K, Akasaka H, Katsuya T, Node K, Fujisawa T, Shimaoka I, et al. (2008).
3335:
3318:
3103:
3086:
2975:
2950:
569:
distribution of these enzymes differs from those of humans making extrapolations from
481:
in most tissues for forming 20-HETE and, concurrently, smaller amounts of 19-hydroxy-5
7575:
7098:
6686:
6609:
6600:
6431:
6200:
6155:
6145:
6090:
6043:
5843:
5793:
5750:
5706:
5663:
5628:
5577:
5536:
5487:
5435:
5397:
5338:
5279:
5232:
5180:
5126:
5091:
5039:
4995:
4959:
4924:
4861:
4819:
4767:
4719:
4646:
4607:
4572:
4520:
4479:
4430:
4375:
4326:
4275:
4240:
4189:
4132:
4097:
4048:
4043:
4008:
3989:
3940:
3899:
3842:
3838:
3807:
3758:
3709:
3660:
3625:
3568:
3522:
3468:
3411:
3376:
3340:
3299:
3264:
3228:
3187:
3143:
3108:
3067:
3021:
2980:
2949:
Valles J, Santos MT, Marcus AJ, Safier LB, Broekman MJ, Islam N, et al. (1993).
2931:
2885:
2836:
2774:
2733:
2692:
2656:
2621:
2586:
2537:
2475:
2429:
2381:
2325:
2276:
2220:
2168:
2164:
2130:
2094:
2059:
1991:
1953:
1897:
1837:
1775:
1740:
1698:
1660:
1616:
1567:
1406:
1398:
1236:
957:
634:
inhibit 20-HETE production; these non-pharmacological agents do so by binding to the
5762:
5675:
5447:
5192:
5138:
5060:
Tesson C, Nawara M, Salih MA, Rossignol R, Zaki MS, Al Balwi M, et al. (2012).
5007:
4779:
4686:
Fava C, Montagnana M, Almgren P, Rosberg L, Lippi G, Hedblad B, et al. (2008).
4442:
4293:
Gainer JV, Bellamine A, Dawson EP, Womble KE, Grant SW, Wang Y, et al. (2005).
4207:
Wen H, Γstman J, Bubb KJ, Panayiotou C, Priestley JV, Baker MD, et al. (2012).
3854:
3580:
3207:"20-hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells"
967:
to promote the entry of ionic calcium into vascular smooth muscle cells through the
246:
7510:
7276:
7114:
6523:
6184:
5868:
5785:
5742:
5718:
5698:
5655:
5618:
5608:
5567:
5526:
5518:
5477:
5427:
5387:
5377:
5328:
5318:
5271:
5224:
5170:
5162:
5118:
5081:
5073:
5031:
4987:
4951:
4914:
4873:
4853:
4809:
4759:
4731:
4709:
4658:
4638:
4599:
4562:
4554:
4510:
4469:
4422:
4365:
4357:
4316:
4267:
4230:
4220:
4179:
4171:
4124:
4087:
4079:
4038:
4028:
3979:
3971:
3930:
3889:
3881:
3834:
3797:
3789:
3748:
3740:
3699:
3691:
3652:
3615:
3607:
3558:
3512:
3504:
3458:
3450:
3403:
3368:
3330:
3291:
3256:
3218:
3179:
3155:
3135:
3098:
3057:
3011:
2970:
2962:
2921:
2875:
2867:
2826:
2816:
2764:
2723:
2684:
2648:
2613:
2576:
2568:
2527:
2519:
2487:
2465:
2419:
2411:
2371:
2363:
2315:
2307:
2266:
2258:
2212:
2180:
2160:
2122:
2086:
2049:
2041:
2003:
1983:
1943:
1935:
1887:
1879:
1827:
1819:
1767:
1732:
1690:
1650:
1606:
1598:
1559:
1441:
1076:
987:
949:
893:
746:
613:
601:
473:
431:
346:
5702:
5659:
4144:
3423:
2908:
Collins XH, Harmon SD, Kaduce TL, Berst KB, Fang X, Moore SA, et al. (2005).
971:; the attendant rise in intracellular calcium triggers these muscles to contract.
596:
Many agents stimulate cells and tissues to produce 20-HETE in vitro and in vivo.
7630:
7550:
7353:
7346:
6748:
6741:
6681:
6593:
6461:
6416:
5963:
5873:
5382:
5323:
4991:
4857:
4558:
4426:
2769:
2751:
Costea I, Mack DR, Lemaitre RN, Israel D, Marcil V, Ahmad A, et al. (2014).
2652:
2523:
2294:
Messina A, Nencioni S, Gervasi PG, Gotlinger KH, Schwartzman ML, Longo V (2010).
1939:
1883:
1637:
Chuang SS, Helvig C, Taimi M, Ramshaw HA, Collop AH, Amad M, et al. (2004).
1268:
1129:
1080:
794:
727:
716:
627:
477:
461:
435:
5035:
4955:
4456:
Mayer B, Lieb W, GΓΆtz A, KΓΆnig IR, Aherrahrou Z, Thiemig A, et al. (2005).
3885:
3656:
3372:
3295:
2090:
1736:
7377:
7292:
7062:
6984:
6691:
6223:
6130:
6100:
5993:
5901:
5275:
5228:
5077:
3744:
3695:
2402:
Garcia V, Cheng J, Weidenhammer A, Ding Y, Wu CC, Zhang F, et al. (2015).
2045:
1514:
1445:
promoting its survival, growth, and vascular endothelial growth factor-induced
1272:
1145:
1021:
998:
953:
886:
754:
750:
742:
700:
617:
605:
505:
can metabolize arachidonic acid to 19-HETE while forming little or no 20-HETE.
389:
79:
20-HETE, 20-Hydroxy-5,8,11,14-eicosatetraenoic, 20-Hydroxyeicosatetraenoic acid
5522:
5431:
5166:
5122:
4763:
2311:
2216:
1694:
1602:
7672:
7610:
7590:
7185:
6900:
6731:
6711:
6441:
6329:
6140:
6013:
5930:
4901:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008).
4796:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008).
3958:
Wu CC, Mei S, Cheng J, Ding Y, Weidenhammer A, Garcia V, et al. (2013).
3678:
Yanes LL, Lima R, Moulana M, Romero DG, Yuan K, Ryan MJ, et al. (2011).
3594:
Orozco LD, Liu H, Perkins E, Johnson DA, Chen BB, Fan F, et al. (2013).
1720:
1229:
1174:
5746:
4271:
4225:
4128:
4007:
Holla VR, Adas F, Imig JD, Zhao X, Price Jr E, Olsen N, et al. (2001).
3935:
3918:
3611:
3454:
3016:
2999:
2728:
2711:
1042:
mouse laboratory model, 20-HETE pretreatment accelerates the development of
7490:
7306:
7266:
7199:
7189:
7180:
7175:
7118:
7076:
6666:
6451:
6360:
6273:
6085:
6080:
5983:
5797:
5754:
5710:
5667:
5632:
5581:
5540:
5491:
5439:
5401:
5342:
5283:
5236:
5184:
5130:
5095:
5043:
4999:
4963:
4928:
4865:
4823:
4814:
4797:
4771:
4723:
4650:
4611:
4576:
4524:
4483:
4434:
4379:
4361:
4330:
4244:
4193:
4158:
Nakagawa K, Holla VR, Wei Y, Wang WH, Gatica A, Wei S, et al. (2006).
4136:
4101:
4052:
4033:
3993:
3975:
3903:
3811:
3762:
3713:
3664:
3629:
3572:
3526:
3472:
3415:
3380:
3303:
3260:
3232:
3223:
3206:
3191:
3183:
3147:
3071:
3025:
2935:
2926:
2909:
2840:
2778:
2737:
2688:
2660:
2625:
2590:
2541:
2479:
2433:
2385:
2329:
2280:
2224:
2172:
2134:
2098:
2063:
1995:
1987:
1957:
1901:
1841:
1771:
1744:
1702:
1664:
1655:
1638:
1620:
1571:
1390:
1364:
1186:
1006:
975:
704:
623:
513:
5554:
Alexanian A, Rufanova VA, Miller B, Flasch A, Roman RJ, Sorokin A (2009).
4279:
3944:
3846:
3508:
3344:
3268:
3112:
2984:
2889:
2696:
1779:
7530:
7458:
7442:
7310:
7282:
7165:
7109:
7052:
7038:
6726:
6721:
6661:
6390:
6375:
6370:
6324:
6263:
6190:
6170:
6149:
6110:
5973:
5938:
5806:
4919:
4902:
2397:
2395:
2345:
2343:
2341:
2339:
1322:
1138:
929:
903:
817:-eicosatetraenoic acid which is also rapidly reduced to 12,20-dihydroxy-5
676:
651:
581:
560:
human breast cancer cell line express messenger RNA for this cytochrome.
2821:
2803:
Jarrar YB, Cha EY, Seo KA, Ghim JL, Kim HJ, Kim DH, et al. (2014).
2470:
2453:
1509:
20-HETE constricts human artery preparations by directly activating the
1308:
The Val433Met variant is also associated with an increased incidence of
1091:(TALH); these effects reduce the absorption of sodium and fluids in the
7520:
7411:
7326:
7316:
7272:
7256:
7252:
7143:
7009:
6877:
6860:
6758:
6604:
6532:
6528:
6475:
6421:
6380:
6205:
6195:
6180:
6048:
5958:
5613:
5175:
3793:
2126:
1429:
1410:
1245:
1166:
1047:
1043:
933:
631:
609:
427:
374:
177:
156:
6914:
6772:
6343:
4626:
4083:
3563:
3546:
2966:
2572:
2454:"Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system"
2392:
2336:
1587:"Cytochrome P450-derived eicosanoids: the neglected pathway in cancer"
7635:
7620:
7615:
7565:
7560:
7205:
7124:
7082:
7072:
6309:
6174:
4976:
4175:
2458:
Journal of Smooth Muscle
Research = Nihon Heikatsukin Gakkai Kikanshi
1418:
1360:
1256:
945:
834:
738:
597:
465:
5851:
1806:
Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC (Jul 2015).
777:-eicosatetraenoic acid which is rapidly reduced to 11,20-dihydroxy-5
544:
mostly expressed in leukocytes, CYP4F3B mostly in the liver. Human
388:
Except where otherwise noted, data are given for materials in their
7570:
7555:
7524:
7514:
7504:
7494:
7475:
7463:
7432:
7427:
7391:
7302:
7155:
7094:
7066:
7056:
7034:
6716:
6701:
6625:
6563:
6548:
6508:
6314:
6289:
6242:
6233:
6160:
6126:
6070:
6065:
6027:
6023:
5997:
5987:
5977:
5967:
5953:
5911:
5505:
Yu W, Chen L, Yang YQ, Falck JR, Guo AM, Li Y, et al. (2011).
3867:
3545:
Capra V, BΓ€ck M, Angiolillo DJ, Cattaneo M, Sakariassen KS (2014).
2752:
1397:
while under expressing message and protein for tissue inhibitor of
659:
508:
The production of 19-HETE with 20-HETE may be significant since 19(
207:
5355:
5296:
5151:
4346:"Association of a CYP4A11 variant and blood pressure in black men"
3437:
Wiest EF, Walsh-Wilcox MT, Rothe M, Schunck WH, Walker MK (2016).
2111:
1194:
124:
7605:
7470:
7436:
7405:
7369:
7227:
7209:
7129:
7086:
7026:
6994:
6804:
6705:
6656:
6629:
6621:
6568:
6502:
6318:
6294:
6215:
6164:
6053:
5916:
3084:
2710:
Curley CR, Monsuur AJ, Wapenaar MC, Rioux JD, Wijmenga C (2006).
2296:"Molecular cloning and enzymatic characterization of sheep CYP2J"
1973:
1264:
1092:
1039:
737:
There are several other pathways that metabolize 20-HETE. Human
696:
647:
585:
549:
532:
233:
4066:
Quigley R, Chakravarty S, Zhao X, Imig JD, Capdevila JH (2009).
3645:
American
Journal of Physiology. Heart and Circulatory Physiology
3284:
American Journal of Physiology. Heart and Circulatory Physiology
2076:
2020:
Yu W, Chai H, Li Y, Zhao H, Xie X, Zheng H, et al. (2012).
1160:
960:
interactions may serve to perpetuate vasoconstrictor responses.
894:
Tissue distribution of 20-HETE-producing enzymes and/or activity
7397:
7373:
7331:
7231:
7159:
6998:
6980:
6838:
6799:
6794:
6572:
6558:
6303:
6219:
6114:
6105:
6095:
6074:
6037:
6008:
6003:
5942:
5934:
5920:
5897:
5645:
4541:
Ding H, Cui G, Zhang L, Xu Y, Bao X, Tu Y, et al. (2010).
2508:"Cytochrome P450 eicosanoids in hypertension and renal disease"
2293:
1458:
1402:
1333:
1026:
928:
to other contracting agents such as alpha adrenergic agonists,
688:
577:
553:
545:
540:
536:
502:
498:
440:
3168:
2673:
1924:"20-HETE and blood pressure regulation: Clinical implications"
1305:
increased arterial stiffness and increased 20-HETE synthesis.
7401:
7137:
7133:
7090:
7004:
6773:
6640:
6617:
6257:
6134:
6017:
5948:
5553:
5466:"20-HETE-producing enzymes are up-regulated in human cancers"
4114:
3436:
2641:
Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics
1584:
1467:
1457:
20-HETE stimulated the proliferation of cultured human brain
1433:
1414:
1206:
663:
655:
557:
501:
may also contribute to the production of these two HETEs and
136:
114:
4685:
2150:
1009:
as well as to the physiological and pathological effects of
263:
7336:
7170:
6915:
6861:
6822:
6513:
6476:
6344:
5463:
5108:
4292:
3544:
3043:
2401:
1805:
1483:
1382:
684:
635:
198:
5059:
4749:
4496:
4065:
3317:
Carroll MA, Sala A, Dunn CE, McGiff JC, Murphy RC (1991).
3085:
Schwartzman ML, Falck JR, Yadagiri P, Escalante B (1989).
2709:
563:
4343:
4257:
2712:"A functional candidate screen for coeliac disease genes"
1922:
Wu CC, Gupta T, Garcia V, Ding Y, Schwartzman ML (2014).
1585:
Panigrahy D, Kaipainen A, Greene ER, Huang S (Dec 2010).
1275:
for large vessel disease stroke risk in this population.
5688:
3726:
2948:
2907:
2750:
1636:
793:-eicosatetraenoic acid; they also metabolize it through
591:
7221:
5024:
Prostaglandins, Leukotrienes, and Essential Fatty Acids
4836:
4206:
3733:
AJP: Regulatory, Integrative and Comparative Physiology
3684:
AJP: Regulatory, Integrative and Comparative Physiology
3593:
3172:
Prostaglandins, Leukotrienes, and Essential Fatty Acids
3125:
2352:"The role of 20-HETE in androgen-mediated hypertension"
2193:
2079:
Prostaglandins, Leukotrienes, and Essential Fatty Acids
1075:
In animal models, 20-HETE stimulates the activation of
4624:
3677:
3491:
Toth P, Rozsa B, Springo Z, Doczi T, Koller A (2011).
3204:
2997:
2146:
2144:
1409:, a proposed drug for treating cancer, cause cultured
1152:
5735:
Journal of Pharmacology and Experimental Therapeutics
4589:
3600:
Journal of Pharmacology and Experimental Therapeutics
3490:
3316:
3281:
2853:
1123:
5838:
5731:
4157:
2554:
5464:Alexanian A, Miller B, Roman RJ, Sorokin A (2012).
4941:
4900:
4795:
4412:
2903:
2901:
2899:
2141:
1107:
1054:indicate that 20-HETE stimulates the activation of
186:
5775:
4455:
3775:
3727:Lima R, Yanes LL, Davis DD, Reckelhoff JF (2013).
2244:
1757:
4006:
3393:
3357:
1921:
1718:
7670:
5594:
3916:
2896:
2802:
670:
245:
5504:
5459:
5457:
5413:
5411:
5252:
5248:
5246:
5205:
5055:
5053:
4791:
4789:
4745:
4743:
4741:
4681:
4679:
4536:
4534:
4013:Proceedings of the National Academy of Sciences
3824:
3540:
3538:
3536:
3486:
3484:
3482:
3039:
3037:
3035:
2501:
2499:
2497:
2447:
2445:
2443:
2240:
2238:
2236:
2234:
2015:
2013:
1969:
1967:
1417:human breast cancer cells to die by triggering
1232:in mice (see above section on genetic models).
1141:, the renin-angiotensin system, and androgens.
642:(UGT) enzymes which metabolize 20-HETE such as
225:acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid
100:
4540:
3957:
3680:"Postmenopausal hypertension: Role of 20-HETE"
2512:Current Opinion in Nephrology and Hypertension
2505:
2115:Alcoholism: Clinical and Experimental Research
1917:
1915:
1913:
1911:
1861:
1859:
1857:
1855:
1853:
1851:
1714:
1712:
1676:
1674:
1632:
1630:
1393:overexpress messenger RNA for and overproduce
1189:-inducing and anti-hypertensive products, the
963:Again in rodent models, 20-HETE acts to block
909:
5822:
4625:Fava C, Ricci M, Melander O, Minuz P (2012).
4350:Journal of the American Society of Nephrology
3964:Journal of the American Society of Nephrology
3497:Journal of Cerebral Blood Flow and Metabolism
2638:
2349:
1801:
1799:
1797:
1795:
1793:
1791:
1789:
1578:
1545:
1543:
1541:
1161:Genetically engineered models of hypertension
5769:
5725:
5682:
5639:
5588:
5547:
5498:
5454:
5408:
5349:
5290:
5243:
5199:
5145:
5102:
5050:
5014:
4970:
4935:
4894:
4830:
4786:
4738:
4676:
4618:
4583:
4531:
4490:
4449:
4406:
4337:
4286:
4200:
4151:
4108:
4059:
4000:
3951:
3861:
3769:
3720:
3671:
3636:
3587:
3533:
3479:
3430:
3387:
3351:
3198:
3162:
3119:
3032:
2998:Thuresson ED, Lakkides KM, Smith WL (2000).
2991:
2796:
2744:
2703:
2632:
2606:Annual Review of Pharmacology and Toxicology
2597:
2548:
2494:
2440:
2287:
2231:
2187:
2105:
2070:
2019:
2010:
1964:
1552:Annual Review of Pharmacology and Toxicology
1482:production blocks the growth of human brain
1339:Researchers have identified at least 3 more
1332:rs1558139 guanine to cytosine variant in an
1252:genotype versus homozygous -845A was 1.42);
857:-eicosatetraenoic acid, then to 18-carboxy-5
497:-eicosatetraenoic acid (19-HETE). However,
5417:
5020:
4251:
3910:
3818:
3310:
3078:
2942:
2847:
2667:
2451:
1908:
1865:
1848:
1709:
1671:
1627:
1095:and thereby tend to reduce blood pressure.
919:
531:In humans, the CYP4 Ο-hydroxylases include
70:)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid
5836:
5829:
5815:
4631:Prostaglandins & Other Lipid Mediators
3642:
3245:
2408:Prostaglandins & Other Lipid Mediators
2356:Prostaglandins & Other Lipid Mediators
2251:Prostaglandins & Other Lipid Mediators
1812:Prostaglandins & Other Lipid Mediators
1786:
1751:
1538:
1525:One study found that 30 patients with the
1033:
278:
164:
5622:
5612:
5571:
5530:
5481:
5391:
5381:
5332:
5322:
5174:
5085:
4918:
4813:
4713:
4703:
4566:
4514:
4473:
4369:
4320:
4310:
4234:
4224:
4183:
4091:
4042:
4032:
3983:
3934:
3893:
3801:
3752:
3703:
3619:
3562:
3516:
3462:
3334:
3239:
3222:
3102:
3061:
3015:
2974:
2925:
2879:
2854:Hill E, Fitzpatrick F, Murphy RC (1992).
2830:
2820:
2768:
2727:
2618:10.1146/annurev.pharmtox.45.120403.100045
2580:
2555:Knights KM, Rowland A, Miners JO (2013).
2531:
2469:
2423:
2375:
2319:
2270:
2053:
1947:
1891:
1831:
1654:
1610:
1564:10.1146/annurev.pharmtox.45.120403.100045
1228:the hypertension associated with Cyp4a14
2603:
2561:British Journal of Clinical Pharmacology
1680:
1549:
434:that has a wide range of effects on the
331:C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCO
2677:Archives of Biochemistry and Biophysics
2245:Capdevila JH, Wang W, Falck JR (2015).
1490:
1222:
885:-hexadecatrrenoic acid, in a series of
564:Production by rodents and other animals
455:
410:, also known as 20-HETE or 20-hydroxy-5
274:
223:
14:
7671:
5111:Journal of Inherited Metabolic Disease
5066:The American Journal of Human Genetics
3917:Stec DE, Mattson DL, Roman RJ (1997).
1278:
1056:Extracellular signal-regulated kinases
1052:human umbilical vein endothelial cells
1016:
745:(s) to form the 20-hydroxy analogs of
644:non-steroidal anti-inflammatory agents
6009:CS gas (2-chlorobenzal malononitrile)
5810:
3551:Journal of Thrombosis and Haemostasis
3361:AJP: Heart and Circulatory Physiology
1976:Drug Metabolism and Drug Interactions
1872:Current Topics in Medicinal Chemistry
1725:AJP: Heart and Circulatory Physiology
1520:
1046:and reduces blood flow caused by the
592:Factors regulating 20-HETE production
303:Key: NNDIXBJHNLFJJP-DTLRTWKJSA-N
144:
5511:Cancer Chemotherapy and Pharmacology
5420:Breast Cancer Research and Treatment
4980:Blood Coagulation & Fibrinolysis
4643:10.1016/j.prostaglandins.2011.11.007
2416:10.1016/j.prostaglandins.2014.12.001
2368:10.1016/j.prostaglandins.2011.06.006
2263:10.1016/j.prostaglandins.2015.05.004
1824:10.1016/j.prostaglandins.2015.03.002
1428:(3'UTRs) of the CYP4Z1 gene and its
1395:vascular endothelial growth factor A
1381:Two human breast cancer cell lines,
1244:in: 512 white males from Tennessee (
965:Calcium-activated potassium channels
741:and other tissues metabolize it via
7581:N-(p-Amylcinnamoyl)anthranilic acid
6697:N-(p-Amylcinnamoyl)anthranilic acid
6437:N-(p-Amylcinnamoyl)anthranilic acid
5790:10.1016/j.freeradbiomed.2008.10.028
5256:Toxicology and Applied Pharmacology
5209:Toxicology and Applied Pharmacology
3776:Lukaszewicz KM, Lombard JH (2013).
3323:The Journal of Biological Chemistry
3091:The Journal of Biological Chemistry
3004:The Journal of Biological Chemistry
2026:Toxicology and Applied Pharmacology
1350:
1200:
1153:Androgen-induced hypertensive model
1070:
584:, metabolizing arachidonic acid to
236:
206:
24:
4715:10.1161/HYPERTENSIONAHA.108.114199
4604:10.1152/physiolgenomics.00003.2007
4516:10.1161/HYPERTENSIONAHA.108.114082
4475:10.1161/01.HYP.0000182658.04299.15
4322:10.1161/01.CIR.0000151309.82473.59
3408:10.1161/01.HYP.0000135658.57547.bb
3140:10.1161/01.CIR.0000136808.72912.D9
3063:10.1161/HYPERTENSIONAHA.107.104463
2872:10.1111/j.1476-5381.1992.tb14327.x
2716:European Journal of Human Genetics
2506:Fan F, Muroya Y, Roman RJ (2015).
1217:
1124:Salt-sensitive hypertension models
1087:and 70 pS K+ channel in the thick
470:Cytochrome P450 omega hydroxylases
25:
7700:
5778:Free Radical Biology and Medicine
4944:Molecular Genetics and Metabolism
4164:Journal of Clinical Investigation
4117:Experimental Biology and Medicine
2955:Journal of Clinical Investigation
1487:are responsible for its actions.
1083:and concurrently also blocks the
914:
667:enzymes and benzene-based drugs.
5470:Cancer Genomics & Proteomics
4907:American Journal of Hypertension
4852:(7): 1495β502, discussion 1502.
3839:10.1097/00004872-199310000-00005
2165:10.1111/j.1365-2559.2010.03606.x
1452:
1426:Three prime untranslated regions
1389:, made to overexpress CYP4Z1 by
1376:
1212:
1108:Spontaneously hypertensive model
573:to humans somewhat complicated.
358:
35:
30:20-Hydroxyeicosatetraenoic acid
5595:Alexanian A, Sorokin A (2013).
4883:from the original on 2019-10-01
4665:from the original on 2024-03-08
4213:Journal of Biological Chemistry
3275:
3211:Journal of Biological Chemistry
2914:Journal of Biological Chemistry
2860:British Journal of Pharmacology
2785:from the original on 2020-07-03
2197:Chemico-Biological Interactions
1643:Journal of Biological Chemistry
1341:single-nucleotide polymorphisms
1118:spontaneously hypertensive rats
1113:Spontaneously hypertensive rats
1098:
1089:Ascending limb of loop of Henle
978:-producing enzyme, endothelial
450:
408:20-Hydroxyeicosatetraenoic acid
392:(at 25 Β°C , 100 kPa).
18:20-hydroxyeicosatetraenoic acid
2350:Wu CC, Schwartzman ML (2011).
1504:
1330:Single-nucleotide polymorphism
1286:single-nucleotide polymorphism
1261:single-nucleotide polymorphism
833:-eicosatetraenoic acid. (The
426:-eicosatetraenoic acid, is an
364:
352:
13:
1:
7655:Receptor/signaling modulators
6004:CR gas (dibenzoxazepine; DBO)
5703:10.1158/0008-5472.can-03-0849
5660:10.1158/1078-0432.CCR-05-0466
4547:Pharmacogenetics and Genomics
3336:10.1016/S0021-9258(18)98897-6
3104:10.1016/S0021-9258(18)80115-6
2809:The Journal of Lipid Research
1808:"Vascular actions of 20-HETE"
1591:Cancer and Metastasis Reviews
1532:
1357:Hereditary spastic paraplegia
942:angiotensin-converting enzyme
902:20-HETE is produced by human
722:
671:Proviso on 20-HETE production
445:Hereditary spastic paraplegia
5383:10.1371/journal.pone.0015647
5324:10.1371/journal.pone.0116247
4992:10.1097/MBC.0000000000000053
4858:10.1097/HJH.0000000000000208
4559:10.1097/FPC.0b013e328336eefe
4427:10.1097/HJH.0b013e3282f2f10c
3249:Biological Mass Spectrometry
2770:10.1053/j.gastro.2013.12.034
2653:10.1016/j.bbapap.2010.09.009
2524:10.1097/MNH.0000000000000088
1940:10.1097/CRD.0b013e3182961659
1884:10.2174/15680266113139990110
1866:Edson KZ, Rettie AE (2013).
1179:Sodiumβhydrogen antiporter 3
1173:Mice depleted of Cyp4a14 by
732:UDP-glucuronosyltransferases
679:) and/or longer chain (e.g.
7:
7283:Paracetamol (acetaminophen)
6191:Paracetamol (acetaminophen)
6061:Farnesyl thiosalicylic acid
5889:15-Deoxy-Ξ-prostaglandin J2
5036:10.1016/j.plefa.2018.02.003
4956:10.1016/j.ymgme.2008.11.161
3886:10.1152/ajprenal.90389.2008
3657:10.1152/ajpheart.00802.2014
3373:10.1152/ajpheart.00627.2003
3296:10.1152/ajpheart.00733.2010
2452:Miyata N, Roman RJ (2005).
2091:10.1016/j.plefa.2010.06.005
1737:10.1152/ajpheart.01172.2007
1058:to cause ERK-dependent and
910:Vascular-related activities
693:5-oxo-eicosatetraenoic acid
640:UDP-glucuronosyltransferase
468:-bound Ο-hydroxylases, the
10:
7705:
5276:10.1016/j.taap.2014.07.018
5229:10.1016/j.taap.2013.05.031
5078:10.1016/j.ajhg.2012.11.001
3745:10.1152/ajpregu.00380.2012
3696:10.1152/ajpregu.00387.2010
2046:10.1016/j.taap.2012.07.019
1464:non-small cell lung cancer
801:)-hydroperoxy-20-hydroxy-5
761:)-hydroperoxy-20-hydroxy-5
709:single nucleotide variants
7648:
7451:
6924:
6913:
6893:
6870:
6859:
6831:
6782:
6771:
6649:
6485:
6474:
6399:
6353:
6342:
6282:
5861:
5850:
5523:10.1007/s00280-010-1521-8
5432:10.1007/s10549-015-3298-2
5167:10.1007/s00415-013-7206-6
5123:10.1007/s10545-014-9759-7
4764:10.1007/s11033-011-0907-y
4752:Molecular Biology Reports
2312:10.3109/00498250903410590
2217:10.1016/j.cbi.2006.01.007
1719:Cheng J, Ou JS, Singh H,
1695:10.1016/j.bcp.2008.03.004
1603:10.1007/s10555-010-9264-x
1438:phosphoinositide 3-kinase
1432:, CYP4Z2P, share several
1371:
1191:Epoxyeicosatrienoic acids
512:)-HETE, although not its
386:
339:
319:
290:
84:
76:
48:
43:
34:
6268:Umbellularia californica
5648:Clinical Cancer Research
4633:(Submitted manuscript).
1683:Biochemical Pharmacology
944:. Other agents such as
938:renin angiotensin system
920:Blood vessel contraction
7238:N-Arachidonoyl dopamine
7020:Andrographis paniculata
5747:10.1124/jpet.105.088567
5601:OncoTargets and Therapy
4846:Journal of Hypertension
4415:Journal of Hypertension
4272:10.1089/dna.1993.12.893
4226:10.1074/jbc.M111.334896
4129:10.1258/ebm.2010.009233
3936:10.1161/01.HYP.29.1.315
3827:Journal of Hypertension
3612:10.1124/jpet.113.203844
3017:10.1074/jbc.275.12.8501
2729:10.1038/sj.ejhg.5201687
1760:Analytical Biochemistry
1134:reactive oxygen species
1034:Blood vessel thrombosis
7659:Ion channel modulators
7388:Tetrahydrocannabivarin
6883:Tripterygium wilfordii
6249:Tetrahydrocannabiorcol
4815:10.1291/hypres.31.1719
4592:Physiological Genomics
4362:10.1681/ASN.2008010063
4034:10.1073/pnas.081627898
3976:10.1681/ASN.2012070714
3443:Toxicological Sciences
3261:10.1002/bms.1200210505
3224:10.1074/jbc.M306849200
3184:10.1054/plef.2000.0138
2927:10.1074/jbc.M504055200
2689:10.1006/abbi.1998.0724
1988:10.1515/dmdi-2011-0037
1772:10.1006/abio.1998.2897
1656:10.1074/jbc.M311830200
1242:essential hypertension
1062:-dependent release of
1060:L-type calcium channel
969:L-type calcium channel
7216:Lysophosphatidic acid
4802:Hypertension Research
3874:AJP: Renal Physiology
3509:10.1038/jcbfm.2011.74
3455:10.1093/toxsci/kfw145
1314:myocardial infarction
1085:Na-K-Cl cotransporter
1064:von Willebrand factor
1025:reduced the vascular
984:heat shock protein 90
980:nitric oxide synthase
7596:Pregnenolone sulfate
7417:Euphorbia resinifera
7359:Euphorbia resinifera
7288:Phenylacetylrinvanil
7248:N-Oleoylethanolamide
7196:Homodihydrocapsaicin
6584:Pregnenolone sulfate
6447:Pregnenolone sulfate
6254:Thiopropanal S-oxide
6239:Tetrahydrocannabinol
5927:Allyl isothiocyanate
5155:Journal of Neurology
4920:10.1038/ajh.2008.276
4260:DNA and Cell Biology
1928:Cardiology in Review
1498:thromboxane receptor
1491:Platelet aggregation
1319:platelet aggregation
1223:CYP4A11 polymorphism
1011:thromboxane receptor
681:docosahexaenoic acid
456:Production in humans
50:Preferred IUPAC name
7501:Cannabigerolic acid
7263:Nordihydrocapsaicin
7224:(acidic conditions)
5560:Anticancer Research
5374:2010PLoSO...515647C
5315:2014PLoSO...9k6247B
5268:2014ToxAP.280...10Z
5221:2013ToxAP.272...37L
4025:2001PNAS...98.5211H
2822:10.1194/jlr.M051169
2471:10.1540/jsmr.41.175
2410:. 116β117: 124β30.
2209:2006CBI...160..204T
2038:2012ToxAP.264...73Y
1310:cerebral infarction
1279:CYP4F2 polymorphism
1017:Blood vessel injury
936:, and a product of
926:smooth muscle cells
382: gΒ·mol
31:
7464:Vernonia tweediana
7043:African blue basil
7015:Bisandrographolide
6601:Steviol glycosides
6554:Hydroxycitronellal
6300:Dehydroligustilide
6120:Angelica acutiloba
6034:Dehydroligustilide
5614:10.2147/OTT.S31586
4398:has generic name (
4072:Nephron Physiology
3794:10.1042/CS20120483
2127:10.1111/acer.12697
1527:metabolic syndrome
1521:Metabolic syndrome
1447:neovascularization
952:compounds such as
604:-inducing agents,
396:Infobox references
29:
7666:
7665:
7644:
7643:
7576:Meclofenamic acid
7382:melegueta peppers
7253:Nonivamide (PAVA)
6989:melegueta peppers
6909:
6908:
6855:
6854:
6767:
6766:
6687:Meclofenamic acid
6610:Stevia rebaudiana
6470:
6469:
6432:Meclofenamic acid
6338:
6337:
6228:melegueta peppers
6201:Phenacyl chloride
6156:N-Methylmaleimide
6146:Methyl salicylate
6091:Hydrogen peroxide
6044:Diallyl disulfide
5906:melegueta peppers
4084:10.1159/000235774
3929:(1 Pt 2): 315β9.
3564:10.1111/jth.12472
2967:10.1172/JCI116709
2573:10.1111/bcp.12086
1407:Isoliquiritigenin
1399:metalloproteinase
1237:gene polymorphism
958:positive feedback
580:, however, is an
476:to 20-HETE by an
404:Chemical compound
402:
401:
259:CompTox Dashboard
126:Interactive image
16:(Redirected from
7696:
7511:Cannabigerovarin
7243:N-Oleoyldopamine
7149:Euodia ruticarpa
7115:Dihydrocapsaicin
6922:
6921:
6918:
6868:
6867:
6864:
6780:
6779:
6776:
6524:Cooling Agent 10
6483:
6482:
6479:
6351:
6350:
6347:
5869:4-Hydroxynonenal
5859:
5858:
5855:
5840:
5831:
5824:
5817:
5808:
5807:
5802:
5801:
5773:
5767:
5766:
5729:
5723:
5722:
5686:
5680:
5679:
5643:
5637:
5636:
5626:
5616:
5592:
5586:
5585:
5575:
5551:
5545:
5544:
5534:
5502:
5496:
5495:
5485:
5461:
5452:
5451:
5415:
5406:
5405:
5395:
5385:
5353:
5347:
5346:
5336:
5326:
5294:
5288:
5287:
5250:
5241:
5240:
5203:
5197:
5196:
5178:
5149:
5143:
5142:
5106:
5100:
5099:
5089:
5057:
5048:
5047:
5018:
5012:
5011:
4974:
4968:
4967:
4939:
4933:
4932:
4922:
4898:
4892:
4891:
4889:
4888:
4882:
4843:
4834:
4828:
4827:
4817:
4793:
4784:
4783:
4747:
4736:
4735:
4717:
4707:
4683:
4674:
4673:
4671:
4670:
4622:
4616:
4615:
4587:
4581:
4580:
4570:
4538:
4529:
4528:
4518:
4494:
4488:
4487:
4477:
4453:
4447:
4446:
4410:
4404:
4403:
4397:
4393:
4391:
4383:
4373:
4341:
4335:
4334:
4324:
4314:
4290:
4284:
4283:
4255:
4249:
4248:
4238:
4228:
4219:(17): 13868β76.
4204:
4198:
4197:
4187:
4176:10.1172/JCI27546
4155:
4149:
4148:
4112:
4106:
4105:
4095:
4063:
4057:
4056:
4046:
4036:
4004:
3998:
3997:
3987:
3955:
3949:
3948:
3938:
3914:
3908:
3907:
3897:
3865:
3859:
3858:
3822:
3816:
3815:
3805:
3782:Clinical Science
3773:
3767:
3766:
3756:
3724:
3718:
3717:
3707:
3675:
3669:
3668:
3651:(11): H1359β67.
3640:
3634:
3633:
3623:
3591:
3585:
3584:
3566:
3542:
3531:
3530:
3520:
3503:(10): 2096β105.
3488:
3477:
3476:
3466:
3434:
3428:
3427:
3391:
3385:
3384:
3355:
3349:
3348:
3338:
3329:(19): 12306β12.
3314:
3308:
3307:
3290:(4): H1194β200.
3279:
3273:
3272:
3243:
3237:
3236:
3226:
3202:
3196:
3195:
3166:
3160:
3159:
3123:
3117:
3116:
3106:
3097:(20): 11658β62.
3082:
3076:
3075:
3065:
3041:
3030:
3029:
3019:
2995:
2989:
2988:
2978:
2946:
2940:
2939:
2929:
2920:(39): 33157β64.
2905:
2894:
2893:
2883:
2851:
2845:
2844:
2834:
2824:
2800:
2794:
2793:
2791:
2790:
2772:
2757:Gastroenterology
2748:
2742:
2741:
2731:
2707:
2701:
2700:
2671:
2665:
2664:
2636:
2630:
2629:
2601:
2595:
2594:
2584:
2552:
2546:
2545:
2535:
2503:
2492:
2491:
2473:
2449:
2438:
2437:
2427:
2399:
2390:
2389:
2379:
2347:
2334:
2333:
2323:
2291:
2285:
2284:
2274:
2242:
2229:
2228:
2191:
2185:
2184:
2148:
2139:
2138:
2109:
2103:
2102:
2074:
2068:
2067:
2057:
2017:
2008:
2007:
1971:
1962:
1961:
1951:
1919:
1906:
1905:
1895:
1863:
1846:
1845:
1835:
1803:
1784:
1783:
1755:
1749:
1748:
1716:
1707:
1706:
1678:
1669:
1668:
1658:
1634:
1625:
1624:
1614:
1582:
1576:
1575:
1547:
1442:MAPK/ERK pathway
1351:CYP2U1 mutations
1201:Other activities
1144:Lewis rats (see
1077:protein kinase C
1071:Renal absorption
988:superoxide anion
950:alpha adrenergic
747:prostaglandin G2
703:) that regulate
616:compounds (e.g.
614:alpha adrenergic
602:vasoconstriction
474:arachidonic acid
432:arachidonic acid
381:
366:
360:
354:
347:Chemical formula
283:
282:
267:
265:
249:
238:
227:
210:
190:
168:
148:
128:
104:
39:
32:
28:
21:
7704:
7703:
7699:
7698:
7697:
7695:
7694:
7693:
7669:
7668:
7667:
7662:
7640:
7631:Tolfenamic acid
7551:Flufenamic acid
7447:
7354:Resiniferatoxin
7347:Ruta graveolens
7110:Diacyl glycerol
6905:
6889:
6851:
6847:
6827:
6813:
6763:
6749:Tolfenamic acid
6742:Ruta graveolens
6682:Flufenamic acid
6645:
6594:Ruta graveolens
6505:(intracellular)
6466:
6462:Tolfenamic acid
6417:Flufenamic acid
6395:
6371:Diacyl glycerol
6334:
6278:
5964:Cannabichromene
5874:4-Oxo-2-nonenal
5846:
5835:
5805:
5774:
5770:
5730:
5726:
5691:Cancer Research
5687:
5683:
5654:(20): 7369β75.
5644:
5640:
5593:
5589:
5566:(10): 3819β24.
5552:
5548:
5503:
5499:
5462:
5455:
5416:
5409:
5354:
5350:
5309:(12): e116247.
5295:
5291:
5251:
5244:
5204:
5200:
5150:
5146:
5107:
5103:
5058:
5051:
5019:
5015:
4975:
4971:
4940:
4936:
4913:(11): 1216β23.
4899:
4895:
4886:
4884:
4880:
4841:
4835:
4831:
4794:
4787:
4748:
4739:
4705:10.1.1.541.9456
4684:
4677:
4668:
4666:
4623:
4619:
4588:
4584:
4539:
4532:
4495:
4491:
4454:
4450:
4411:
4407:
4395:
4394:
4385:
4384:
4342:
4338:
4312:10.1.1.335.1764
4291:
4287:
4256:
4252:
4205:
4201:
4170:(6): 1696β702.
4156:
4152:
4123:(11): 1365β74.
4113:
4109:
4064:
4060:
4005:
4001:
3956:
3952:
3915:
3911:
3866:
3862:
3823:
3819:
3788:(12): 695β700.
3774:
3770:
3725:
3721:
3676:
3672:
3641:
3637:
3592:
3588:
3543:
3534:
3489:
3480:
3435:
3431:
3392:
3388:
3367:(3): H1089β95.
3356:
3352:
3315:
3311:
3280:
3276:
3244:
3240:
3203:
3199:
3167:
3163:
3124:
3120:
3083:
3079:
3042:
3033:
2996:
2992:
2947:
2943:
2906:
2897:
2852:
2848:
2815:(11): 2334β42.
2801:
2797:
2788:
2786:
2749:
2745:
2722:(11): 1215β22.
2708:
2704:
2672:
2668:
2637:
2633:
2602:
2598:
2553:
2549:
2504:
2495:
2450:
2441:
2400:
2393:
2348:
2337:
2292:
2288:
2243:
2232:
2192:
2188:
2149:
2142:
2110:
2106:
2075:
2071:
2018:
2011:
1972:
1965:
1920:
1909:
1878:(12): 1429β40.
1864:
1849:
1804:
1787:
1756:
1752:
1731:(2): H1018β26.
1717:
1710:
1689:(12): 2263β75.
1679:
1672:
1635:
1628:
1583:
1579:
1548:
1539:
1535:
1523:
1507:
1493:
1455:
1379:
1374:
1353:
1281:
1269:ischemic stroke
1225:
1220:
1218:Genetic studies
1215:
1203:
1163:
1155:
1130:sodium chloride
1126:
1110:
1101:
1073:
1036:
1019:
1013:-activation .
922:
917:
912:
896:
795:12-lipoxygenase
728:Glucuronidation
725:
717:Coeliac disease
713:Krohn's disease
673:
628:carbon monoxide
594:
566:
528:stereoisomers.
478:omega oxidation
462:Cytochrome P450
458:
453:
436:vascular system
405:
398:
393:
379:
369:
363:
357:
349:
335:
332:
327:
326:
315:
312:
311:
305:
304:
298:
297:
286:
276:DTXSID601009895
268:
261:
252:
239:
213:
193:
180:
171:
151:
131:
118:
107:
94:
80:
72:
71:
23:
22:
15:
12:
11:
5:
7702:
7692:
7691:
7686:
7681:
7664:
7663:
7649:
7646:
7645:
7642:
7641:
7639:
7638:
7633:
7628:
7623:
7618:
7613:
7608:
7603:
7598:
7593:
7588:
7583:
7578:
7573:
7568:
7563:
7558:
7553:
7548:
7543:
7538:
7533:
7528:
7518:
7508:
7498:
7488:
7483:
7478:
7473:
7468:
7455:
7453:
7449:
7448:
7446:
7445:
7440:
7430:
7425:
7409:
7395:
7385:
7367:
7351:
7339:
7334:
7329:
7324:
7321:Dorrigo pepper
7314:
7300:
7293:Phorbol esters
7290:
7285:
7280:
7270:
7260:
7250:
7245:
7240:
7235:
7225:
7218:
7213:
7203:
7193:
7183:
7178:
7173:
7168:
7163:
7153:
7141:
7127:
7122:
7112:
7107:
7102:
7080:
7070:
7063:Cannabidivarin
7060:
7050:
7031:camphor laurel
7024:
7012:
7007:
7002:
6992:
6974:
6969:
6964:
6959:
6954:
6949:
6944:
6939:
6934:
6928:
6926:
6919:
6911:
6910:
6907:
6906:
6904:
6903:
6897:
6895:
6891:
6890:
6888:
6887:
6874:
6872:
6865:
6857:
6856:
6853:
6852:
6850:
6849:
6845:
6841:
6835:
6833:
6829:
6828:
6826:
6825:
6820:
6815:
6811:
6807:
6802:
6797:
6792:
6786:
6784:
6777:
6769:
6768:
6765:
6764:
6762:
6761:
6756:
6751:
6746:
6734:
6729:
6724:
6719:
6714:
6709:
6699:
6694:
6692:Mefenamic acid
6689:
6684:
6679:
6674:
6669:
6664:
6659:
6653:
6651:
6647:
6646:
6644:
6643:
6638:
6633:
6614:
6598:
6586:
6581:
6576:
6566:
6561:
6556:
6551:
6546:
6541:
6536:
6526:
6521:
6516:
6511:
6506:
6500:
6495:
6489:
6487:
6480:
6472:
6471:
6468:
6467:
6465:
6464:
6459:
6454:
6449:
6444:
6439:
6434:
6429:
6424:
6419:
6414:
6409:
6403:
6401:
6397:
6396:
6394:
6393:
6388:
6385:St John's wort
6378:
6373:
6368:
6365:St John's wort
6357:
6355:
6348:
6340:
6339:
6336:
6335:
6333:
6332:
6327:
6322:
6312:
6307:
6297:
6292:
6286:
6284:
6280:
6279:
6277:
6276:
6271:
6261:
6251:
6246:
6236:
6231:
6213:
6210:Dorrigo pepper
6203:
6198:
6193:
6188:
6178:
6168:
6158:
6153:
6143:
6138:
6131:Sichuan pepper
6124:
6108:
6103:
6101:Isothiocyanate
6098:
6093:
6088:
6083:
6078:
6068:
6063:
6058:
6046:
6041:
6031:
6021:
6011:
6006:
6001:
5994:Cinnamaldehyde
5991:
5981:
5971:
5961:
5956:
5951:
5946:
5924:
5914:
5909:
5891:
5886:
5881:
5876:
5871:
5865:
5863:
5856:
5848:
5847:
5834:
5833:
5826:
5819:
5811:
5804:
5803:
5768:
5724:
5697:(7): 2357β64.
5681:
5638:
5587:
5546:
5497:
5453:
5407:
5368:(12): e15647.
5348:
5289:
5242:
5198:
5144:
5101:
5072:(6): 1051β64.
5049:
5013:
4969:
4934:
4893:
4829:
4808:(9): 1719β26.
4785:
4758:(2): 1677β82.
4737:
4675:
4637:(3β4): 75β85.
4617:
4582:
4530:
4489:
4448:
4405:
4356:(8): 1606β12.
4336:
4285:
4250:
4199:
4150:
4107:
4058:
3999:
3970:(8): 1288β96.
3950:
3909:
3860:
3833:(10): 1031β8.
3817:
3768:
3739:(3): R248β51.
3719:
3690:(6): R1543β8.
3670:
3635:
3586:
3532:
3478:
3429:
3386:
3350:
3309:
3274:
3238:
3217:(4): 2648β56.
3197:
3161:
3118:
3077:
3031:
3010:(12): 8501β7.
2990:
2961:(3): 1357β65.
2941:
2895:
2846:
2795:
2743:
2702:
2666:
2631:
2596:
2567:(4): 587β602.
2547:
2493:
2439:
2391:
2362:(1β4): 45β53.
2335:
2286:
2230:
2186:
2153:Histopathology
2140:
2104:
2069:
2009:
1963:
1907:
1847:
1785:
1750:
1708:
1670:
1649:(8): 6305β14.
1626:
1577:
1536:
1534:
1531:
1522:
1519:
1515:thromboxane A2
1506:
1503:
1492:
1489:
1454:
1451:
1378:
1375:
1373:
1370:
1352:
1349:
1280:
1277:
1273:genetic marker
1224:
1221:
1219:
1216:
1214:
1211:
1202:
1199:
1162:
1159:
1154:
1151:
1146:Laboratory rat
1125:
1122:
1109:
1106:
1100:
1097:
1072:
1069:
1035:
1032:
1022:Sprague Dawley
1018:
1015:
999:thromboxane A2
954:norepinephrine
921:
918:
916:
915:Rodent studies
913:
911:
908:
895:
892:
887:Beta oxidation
755:thromboxane B2
751:thromboxane A2
743:cyclooxygenase
730:of 20-HETE by
724:
721:
701:prostaglandins
699:, and several
672:
669:
662:, and various
618:norepinephrine
606:angiotensin II
593:
590:
571:rodent studies
565:
562:
457:
454:
452:
449:
430:metabolite of
403:
400:
399:
394:
390:standard state
387:
384:
383:
377:
371:
370:
367:
361:
355:
350:
345:
342:
341:
337:
336:
334:
333:
330:
322:
321:
320:
317:
316:
314:
313:
309:
308:
306:
302:
301:
293:
292:
291:
288:
287:
285:
284:
271:
269:
257:
254:
253:
251:
250:
242:
240:
232:
229:
228:
221:
215:
214:
212:
211:
203:
201:
195:
194:
192:
191:
183:
181:
176:
173:
172:
170:
169:
161:
159:
153:
152:
150:
149:
141:
139:
133:
132:
130:
129:
121:
119:
112:
109:
108:
106:
105:
97:
95:
90:
87:
86:
82:
81:
78:
74:
73:
53:
52:
46:
45:
41:
40:
9:
6:
4:
3:
2:
7701:
7690:
7687:
7685:
7682:
7680:
7677:
7676:
7674:
7661:
7660:
7656:
7653:
7647:
7637:
7634:
7632:
7629:
7627:
7624:
7622:
7619:
7617:
7614:
7612:
7611:Ruthenium red
7609:
7607:
7604:
7602:
7599:
7597:
7594:
7592:
7591:Niflumic acid
7589:
7587:
7584:
7582:
7579:
7577:
7574:
7572:
7569:
7567:
7564:
7562:
7559:
7557:
7554:
7552:
7549:
7547:
7544:
7542:
7539:
7537:
7534:
7532:
7529:
7526:
7522:
7519:
7516:
7512:
7509:
7506:
7502:
7499:
7496:
7492:
7489:
7487:
7484:
7482:
7479:
7477:
7474:
7472:
7469:
7466:
7465:
7460:
7459:Ξ±-Spinasterol
7457:
7456:
7454:
7450:
7444:
7441:
7438:
7434:
7431:
7429:
7426:
7423:
7422:
7418:
7413:
7410:
7407:
7403:
7399:
7396:
7393:
7389:
7386:
7383:
7379:
7375:
7371:
7368:
7365:
7364:
7360:
7355:
7352:
7349:
7348:
7343:
7340:
7338:
7335:
7333:
7330:
7328:
7325:
7322:
7318:
7315:
7312:
7308:
7304:
7301:
7298:
7294:
7291:
7289:
7286:
7284:
7281:
7278:
7274:
7271:
7268:
7264:
7261:
7258:
7254:
7251:
7249:
7246:
7244:
7241:
7239:
7236:
7233:
7229:
7226:
7223:
7219:
7217:
7214:
7211:
7207:
7204:
7201:
7197:
7194:
7191:
7187:
7186:Homocapsaicin
7184:
7182:
7179:
7177:
7174:
7172:
7169:
7167:
7164:
7161:
7157:
7154:
7151:
7150:
7145:
7142:
7139:
7135:
7131:
7128:
7126:
7123:
7120:
7116:
7113:
7111:
7108:
7106:
7103:
7100:
7099:wild bergamot
7096:
7092:
7088:
7084:
7081:
7078:
7074:
7071:
7068:
7064:
7061:
7058:
7054:
7051:
7048:
7047:camphor basil
7044:
7040:
7036:
7032:
7028:
7025:
7022:
7021:
7016:
7013:
7011:
7008:
7006:
7003:
7000:
6996:
6993:
6990:
6986:
6982:
6978:
6975:
6973:
6970:
6968:
6965:
6963:
6960:
6958:
6955:
6953:
6950:
6948:
6945:
6943:
6940:
6938:
6935:
6933:
6930:
6929:
6927:
6923:
6920:
6917:
6912:
6902:
6901:Ruthenium red
6899:
6898:
6896:
6892:
6885:
6884:
6879:
6876:
6875:
6873:
6869:
6866:
6863:
6858:
6848:
6842:
6840:
6837:
6836:
6834:
6830:
6824:
6821:
6819:
6816:
6814:
6808:
6806:
6803:
6801:
6798:
6796:
6793:
6791:
6788:
6787:
6785:
6781:
6778:
6775:
6770:
6760:
6757:
6755:
6752:
6750:
6747:
6744:
6743:
6738:
6735:
6733:
6732:Ruthenium red
6730:
6728:
6725:
6723:
6720:
6718:
6715:
6713:
6712:Niflumic acid
6710:
6707:
6703:
6700:
6698:
6695:
6693:
6690:
6688:
6685:
6683:
6680:
6678:
6675:
6673:
6670:
6668:
6665:
6663:
6660:
6658:
6655:
6654:
6652:
6648:
6642:
6639:
6637:
6634:
6632:; indirectly)
6631:
6627:
6623:
6619:
6615:
6612:
6611:
6606:
6602:
6599:
6596:
6595:
6590:
6587:
6585:
6582:
6580:
6577:
6574:
6570:
6567:
6565:
6562:
6560:
6557:
6555:
6552:
6550:
6547:
6545:
6542:
6540:
6539:Frescolat MGA
6537:
6534:
6530:
6527:
6525:
6522:
6520:
6517:
6515:
6512:
6510:
6507:
6504:
6501:
6499:
6496:
6494:
6491:
6490:
6488:
6484:
6481:
6478:
6473:
6463:
6460:
6458:
6455:
6453:
6450:
6448:
6445:
6443:
6442:Niflumic acid
6440:
6438:
6435:
6433:
6430:
6428:
6425:
6423:
6420:
6418:
6415:
6413:
6410:
6408:
6405:
6404:
6402:
6398:
6392:
6389:
6386:
6382:
6379:
6377:
6374:
6372:
6369:
6366:
6362:
6359:
6358:
6356:
6352:
6349:
6346:
6341:
6331:
6330:Ruthenium red
6328:
6326:
6323:
6320:
6316:
6313:
6311:
6308:
6305:
6301:
6298:
6296:
6293:
6291:
6288:
6287:
6285:
6281:
6275:
6272:
6269:
6265:
6262:
6259:
6255:
6252:
6250:
6247:
6244:
6240:
6237:
6235:
6232:
6229:
6225:
6221:
6217:
6214:
6211:
6207:
6204:
6202:
6199:
6197:
6194:
6192:
6189:
6186:
6182:
6179:
6176:
6172:
6169:
6166:
6162:
6159:
6157:
6154:
6151:
6147:
6144:
6142:
6141:Methylglyoxal
6139:
6136:
6132:
6128:
6125:
6122:
6121:
6116:
6112:
6109:
6107:
6104:
6102:
6099:
6097:
6094:
6092:
6089:
6087:
6084:
6082:
6079:
6076:
6072:
6069:
6067:
6064:
6062:
6059:
6056:
6055:
6050:
6047:
6045:
6042:
6039:
6035:
6032:
6029:
6025:
6022:
6019:
6015:
6014:Cuminaldehyde
6012:
6010:
6007:
6005:
6002:
5999:
5995:
5992:
5989:
5985:
5982:
5979:
5975:
5972:
5969:
5965:
5962:
5960:
5957:
5955:
5952:
5950:
5947:
5944:
5940:
5936:
5932:
5928:
5925:
5922:
5918:
5915:
5913:
5910:
5907:
5903:
5899:
5895:
5892:
5890:
5887:
5885:
5882:
5880:
5877:
5875:
5872:
5870:
5867:
5866:
5864:
5860:
5857:
5854:
5849:
5845:
5842:
5832:
5827:
5825:
5820:
5818:
5813:
5812:
5809:
5799:
5795:
5791:
5787:
5784:(2): 263β70.
5783:
5779:
5772:
5764:
5760:
5756:
5752:
5748:
5744:
5741:(2): 526β33.
5740:
5736:
5728:
5720:
5716:
5712:
5708:
5704:
5700:
5696:
5692:
5685:
5677:
5673:
5669:
5665:
5661:
5657:
5653:
5649:
5642:
5634:
5630:
5625:
5620:
5615:
5610:
5606:
5602:
5598:
5591:
5583:
5579:
5574:
5569:
5565:
5561:
5557:
5550:
5542:
5538:
5533:
5528:
5524:
5520:
5517:(3): 619β29.
5516:
5512:
5508:
5501:
5493:
5489:
5484:
5479:
5475:
5471:
5467:
5460:
5458:
5449:
5445:
5441:
5437:
5433:
5429:
5426:(1): 105β18.
5425:
5421:
5414:
5412:
5403:
5399:
5394:
5389:
5384:
5379:
5375:
5371:
5367:
5363:
5359:
5352:
5344:
5340:
5335:
5330:
5325:
5320:
5316:
5312:
5308:
5304:
5300:
5293:
5285:
5281:
5277:
5273:
5269:
5265:
5261:
5257:
5249:
5247:
5238:
5234:
5230:
5226:
5222:
5218:
5214:
5210:
5202:
5194:
5190:
5186:
5182:
5177:
5172:
5168:
5164:
5161:(2): 373β81.
5160:
5156:
5148:
5140:
5136:
5132:
5128:
5124:
5120:
5117:(1): 99β110.
5116:
5112:
5105:
5097:
5093:
5088:
5083:
5079:
5075:
5071:
5067:
5063:
5056:
5054:
5045:
5041:
5037:
5033:
5029:
5025:
5017:
5009:
5005:
5001:
4997:
4993:
4989:
4986:(4): 369β74.
4985:
4981:
4973:
4965:
4961:
4957:
4953:
4949:
4945:
4938:
4930:
4926:
4921:
4916:
4912:
4908:
4904:
4897:
4879:
4875:
4871:
4867:
4863:
4859:
4855:
4851:
4847:
4840:
4833:
4825:
4821:
4816:
4811:
4807:
4803:
4799:
4792:
4790:
4781:
4777:
4773:
4769:
4765:
4761:
4757:
4753:
4746:
4744:
4742:
4733:
4729:
4725:
4721:
4716:
4711:
4706:
4701:
4698:(2): 373β80.
4697:
4693:
4689:
4682:
4680:
4664:
4660:
4656:
4652:
4648:
4644:
4640:
4636:
4632:
4628:
4621:
4613:
4609:
4605:
4601:
4597:
4593:
4586:
4578:
4574:
4569:
4564:
4560:
4556:
4553:(3): 187β94.
4552:
4548:
4544:
4537:
4535:
4526:
4522:
4517:
4512:
4509:(6): 1142β8.
4508:
4504:
4500:
4493:
4485:
4481:
4476:
4471:
4468:(4): 766β71.
4467:
4463:
4459:
4452:
4444:
4440:
4436:
4432:
4428:
4424:
4421:(3): 453β61.
4420:
4416:
4409:
4401:
4396:|first8=
4389:
4381:
4377:
4372:
4367:
4363:
4359:
4355:
4351:
4347:
4340:
4332:
4328:
4323:
4318:
4313:
4308:
4304:
4300:
4296:
4289:
4281:
4277:
4273:
4269:
4266:(10): 893β9.
4265:
4261:
4254:
4246:
4242:
4237:
4232:
4227:
4222:
4218:
4214:
4210:
4203:
4195:
4191:
4186:
4181:
4177:
4173:
4169:
4165:
4161:
4154:
4146:
4142:
4138:
4134:
4130:
4126:
4122:
4118:
4111:
4103:
4099:
4094:
4089:
4085:
4081:
4077:
4073:
4069:
4062:
4054:
4050:
4045:
4040:
4035:
4030:
4026:
4022:
4019:(9): 5211β6.
4018:
4014:
4010:
4003:
3995:
3991:
3986:
3981:
3977:
3973:
3969:
3965:
3961:
3954:
3946:
3942:
3937:
3932:
3928:
3924:
3920:
3913:
3905:
3901:
3896:
3891:
3887:
3883:
3880:(4): F771β9.
3879:
3875:
3871:
3864:
3856:
3852:
3848:
3844:
3840:
3836:
3832:
3828:
3821:
3813:
3809:
3804:
3799:
3795:
3791:
3787:
3783:
3779:
3772:
3764:
3760:
3755:
3750:
3746:
3742:
3738:
3734:
3730:
3723:
3715:
3711:
3706:
3701:
3697:
3693:
3689:
3685:
3681:
3674:
3666:
3662:
3658:
3654:
3650:
3646:
3639:
3631:
3627:
3622:
3617:
3613:
3609:
3605:
3601:
3597:
3590:
3582:
3578:
3574:
3570:
3565:
3560:
3557:(2): 126β37.
3556:
3552:
3548:
3541:
3539:
3537:
3528:
3524:
3519:
3514:
3510:
3506:
3502:
3498:
3494:
3487:
3485:
3483:
3474:
3470:
3465:
3460:
3456:
3452:
3448:
3444:
3440:
3433:
3425:
3421:
3417:
3413:
3409:
3405:
3401:
3397:
3390:
3382:
3378:
3374:
3370:
3366:
3362:
3354:
3346:
3342:
3337:
3332:
3328:
3324:
3320:
3313:
3305:
3301:
3297:
3293:
3289:
3285:
3278:
3270:
3266:
3262:
3258:
3255:(5): 249β53.
3254:
3250:
3242:
3234:
3230:
3225:
3220:
3216:
3212:
3208:
3201:
3193:
3189:
3185:
3181:
3178:(3): 175β81.
3177:
3173:
3165:
3157:
3153:
3149:
3145:
3141:
3137:
3134:(4): 438β43.
3133:
3129:
3122:
3114:
3110:
3105:
3100:
3096:
3092:
3088:
3081:
3073:
3069:
3064:
3059:
3056:(5): 1393β8.
3055:
3051:
3047:
3040:
3038:
3036:
3027:
3023:
3018:
3013:
3009:
3005:
3001:
2994:
2986:
2982:
2977:
2972:
2968:
2964:
2960:
2956:
2952:
2945:
2937:
2933:
2928:
2923:
2919:
2915:
2911:
2904:
2902:
2900:
2891:
2887:
2882:
2877:
2873:
2869:
2866:(2): 267β74.
2865:
2861:
2857:
2850:
2842:
2838:
2833:
2828:
2823:
2818:
2814:
2810:
2806:
2799:
2784:
2780:
2776:
2771:
2766:
2763:(4): 929β31.
2762:
2758:
2754:
2747:
2739:
2735:
2730:
2725:
2721:
2717:
2713:
2706:
2698:
2694:
2690:
2686:
2682:
2678:
2670:
2662:
2658:
2654:
2650:
2647:(1): 210β22.
2646:
2642:
2635:
2627:
2623:
2619:
2615:
2611:
2607:
2600:
2592:
2588:
2583:
2578:
2574:
2570:
2566:
2562:
2558:
2551:
2543:
2539:
2534:
2529:
2525:
2521:
2517:
2513:
2509:
2502:
2500:
2498:
2489:
2485:
2481:
2477:
2472:
2467:
2464:(4): 175β93.
2463:
2459:
2455:
2448:
2446:
2444:
2435:
2431:
2426:
2421:
2417:
2413:
2409:
2405:
2398:
2396:
2387:
2383:
2378:
2373:
2369:
2365:
2361:
2357:
2353:
2346:
2344:
2342:
2340:
2331:
2327:
2322:
2317:
2313:
2309:
2306:(2): 109β18.
2305:
2301:
2297:
2290:
2282:
2278:
2273:
2268:
2264:
2260:
2256:
2252:
2248:
2241:
2239:
2237:
2235:
2226:
2222:
2218:
2214:
2210:
2206:
2203:(3): 204β16.
2202:
2198:
2190:
2182:
2178:
2174:
2170:
2166:
2162:
2159:(2): 202β11.
2158:
2154:
2147:
2145:
2136:
2132:
2128:
2124:
2120:
2116:
2108:
2100:
2096:
2092:
2088:
2085:(2): 105β10.
2084:
2080:
2073:
2065:
2061:
2056:
2051:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2016:
2014:
2005:
2001:
1997:
1993:
1989:
1985:
1981:
1977:
1970:
1968:
1959:
1955:
1950:
1945:
1941:
1937:
1933:
1929:
1925:
1918:
1916:
1914:
1912:
1903:
1899:
1894:
1889:
1885:
1881:
1877:
1873:
1869:
1862:
1860:
1858:
1856:
1854:
1852:
1843:
1839:
1834:
1829:
1825:
1821:
1817:
1813:
1809:
1802:
1800:
1798:
1796:
1794:
1792:
1790:
1781:
1777:
1773:
1769:
1765:
1761:
1754:
1746:
1742:
1738:
1734:
1730:
1726:
1722:
1715:
1713:
1704:
1700:
1696:
1692:
1688:
1684:
1677:
1675:
1666:
1662:
1657:
1652:
1648:
1644:
1640:
1633:
1631:
1622:
1618:
1613:
1608:
1604:
1600:
1597:(4): 723β35.
1596:
1592:
1588:
1581:
1573:
1569:
1565:
1561:
1557:
1553:
1546:
1544:
1542:
1537:
1530:
1528:
1518:
1516:
1512:
1502:
1499:
1488:
1485:
1479:
1475:
1473:
1469:
1465:
1460:
1453:Other cancers
1450:
1448:
1443:
1439:
1435:
1431:
1427:
1422:
1420:
1416:
1412:
1408:
1404:
1400:
1396:
1392:
1388:
1384:
1377:Breast cancer
1369:
1366:
1362:
1358:
1348:
1346:
1342:
1337:
1335:
1331:
1326:
1324:
1321:responses to
1320:
1315:
1311:
1306:
1303:
1299:
1295:
1291:
1287:
1276:
1274:
1270:
1266:
1262:
1258:
1253:
1249:
1247:
1243:
1238:
1233:
1231:
1230:gene knockout
1213:Human studies
1210:
1208:
1198:
1196:
1192:
1188:
1182:
1180:
1176:
1175:gene knockout
1171:
1168:
1158:
1150:
1147:
1142:
1140:
1135:
1131:
1121:
1119:
1114:
1105:
1096:
1094:
1090:
1086:
1082:
1081:Na+/K+-ATPase
1078:
1068:
1065:
1061:
1057:
1053:
1049:
1045:
1041:
1031:
1028:
1023:
1014:
1012:
1008:
1002:
1000:
996:
991:
989:
985:
981:
977:
972:
970:
966:
961:
959:
955:
951:
947:
943:
939:
935:
931:
927:
907:
905:
900:
891:
888:
884:
880:
876:
872:
868:
864:
860:
856:
852:
848:
844:
839:
836:
832:
828:
824:
820:
816:
812:
808:
804:
800:
796:
792:
788:
784:
780:
776:
772:
768:
764:
760:
756:
752:
748:
744:
740:
735:
733:
729:
720:
718:
714:
710:
706:
702:
698:
694:
690:
686:
682:
678:
668:
665:
661:
657:
653:
649:
645:
641:
637:
633:
629:
625:
621:
619:
615:
611:
607:
603:
599:
589:
587:
583:
579:
574:
572:
561:
559:
555:
551:
547:
542:
538:
534:
529:
527:
523:
519:
515:
511:
506:
504:
500:
496:
492:
488:
484:
479:
475:
472:, metabolize
471:
467:
463:
448:
446:
442:
437:
433:
429:
425:
421:
417:
413:
409:
397:
391:
385:
378:
376:
373:
372:
351:
348:
344:
343:
338:
329:
328:
325:
318:
307:
300:
299:
296:
289:
281:
277:
273:
272:
270:
260:
256:
255:
248:
244:
243:
241:
235:
231:
230:
226:
222:
220:
217:
216:
209:
205:
204:
202:
200:
197:
196:
189:
185:
184:
182:
179:
175:
174:
167:
163:
162:
160:
158:
155:
154:
147:
143:
142:
140:
138:
135:
134:
127:
123:
122:
120:
116:
111:
110:
103:
99:
98:
96:
93:
89:
88:
83:
75:
69:
65:
61:
57:
51:
47:
42:
38:
33:
27:
19:
7679:Cell biology
7651:
7650:
7491:Cannabigerol
7462:
7415:
7357:
7345:
7307:black pepper
7267:chili pepper
7200:chili pepper
7190:chili pepper
7181:Hepoxilin B3
7176:Hepoxilin A3
7147:
7119:chili pepper
7077:chili pepper
7018:
6971:
6881:
6740:
6667:Clotrimazole
6608:
6592:
6544:Frescolat ML
6452:Progesterone
6361:Adhyperforin
6274:WIN 55,212-2
6267:
6118:
6086:Hepoxilin B3
6081:Hepoxilin A3
6052:
5984:Cannabigerol
5781:
5777:
5771:
5738:
5734:
5727:
5694:
5690:
5684:
5651:
5647:
5641:
5604:
5600:
5590:
5563:
5559:
5549:
5514:
5510:
5500:
5476:(4): 163β9.
5473:
5469:
5423:
5419:
5365:
5361:
5351:
5306:
5302:
5292:
5262:(1): 10β20.
5259:
5255:
5215:(1): 37β48.
5212:
5208:
5201:
5158:
5154:
5147:
5114:
5110:
5104:
5069:
5065:
5027:
5023:
5016:
4983:
4979:
4972:
4950:(3): 145β7.
4947:
4943:
4937:
4910:
4906:
4896:
4885:. Retrieved
4849:
4845:
4832:
4805:
4801:
4755:
4751:
4695:
4692:Hypertension
4691:
4667:. Retrieved
4634:
4630:
4620:
4598:(1): 74β81.
4595:
4591:
4585:
4550:
4546:
4506:
4503:Hypertension
4502:
4492:
4465:
4462:Hypertension
4461:
4451:
4418:
4414:
4408:
4388:cite journal
4353:
4349:
4339:
4302:
4298:
4288:
4263:
4259:
4253:
4216:
4212:
4202:
4167:
4163:
4153:
4120:
4116:
4110:
4075:
4071:
4061:
4016:
4012:
4002:
3967:
3963:
3953:
3926:
3923:Hypertension
3922:
3912:
3877:
3873:
3863:
3830:
3826:
3820:
3785:
3781:
3771:
3736:
3732:
3722:
3687:
3683:
3673:
3648:
3644:
3638:
3606:(1): 67β74.
3603:
3599:
3589:
3554:
3550:
3500:
3496:
3449:(1): 43β54.
3446:
3442:
3432:
3402:(2): 210β6.
3399:
3396:Hypertension
3395:
3389:
3364:
3360:
3353:
3326:
3322:
3312:
3287:
3283:
3277:
3252:
3248:
3241:
3214:
3210:
3200:
3175:
3171:
3164:
3131:
3127:
3121:
3094:
3090:
3080:
3053:
3050:Hypertension
3049:
3007:
3003:
2993:
2958:
2954:
2944:
2917:
2913:
2863:
2859:
2849:
2812:
2808:
2798:
2787:. Retrieved
2760:
2756:
2746:
2719:
2715:
2705:
2683:(2): 201β5.
2680:
2676:
2669:
2644:
2640:
2634:
2609:
2605:
2599:
2564:
2560:
2550:
2518:(1): 37β46.
2515:
2511:
2461:
2457:
2407:
2359:
2355:
2303:
2299:
2289:
2254:
2250:
2200:
2196:
2189:
2156:
2152:
2121:(5): 790β7.
2118:
2114:
2107:
2082:
2078:
2072:
2032:(1): 73β83.
2029:
2025:
1982:(2): 63β71.
1979:
1975:
1931:
1927:
1875:
1871:
1815:
1811:
1766:(1): 55β68.
1763:
1759:
1753:
1728:
1724:
1686:
1682:
1646:
1642:
1594:
1590:
1580:
1555:
1551:
1524:
1508:
1494:
1480:
1476:
1456:
1423:
1391:transfection
1380:
1365:mitochondria
1354:
1344:
1338:
1327:
1307:
1301:
1297:
1293:
1289:
1282:
1254:
1250:
1234:
1226:
1204:
1187:vasodilation
1183:
1172:
1164:
1156:
1143:
1127:
1111:
1102:
1099:Hypertension
1074:
1037:
1020:
1007:hypertension
1003:
992:
982:(eNOS) with
976:nitric oxide
973:
962:
923:
901:
897:
882:
878:
874:
870:
866:
862:
858:
854:
850:
846:
842:
840:
830:
826:
822:
818:
814:
810:
806:
802:
798:
790:
786:
782:
778:
774:
770:
766:
762:
758:
736:
726:
705:inflammation
674:
624:Nitric oxide
622:
595:
575:
567:
530:
525:
521:
517:
514:stereoisomer
509:
507:
494:
490:
486:
482:
460:A subset of
459:
451:Biosynthesis
423:
419:
415:
411:
407:
406:
85:Identifiers
77:Other names
67:
63:
59:
55:
26:
7689:Eicosanoids
7684:Fatty acids
7626:Tivanisiran
7531:Capsazepine
7443:Zucapsaicin
7311:long pepper
7277:Pacific yew
7166:GSK1016790A
7053:Cannabidiol
7039:camphorweed
6727:RQ-00203078
6722:PF-05105679
6662:Capsazepine
6427:GSK2293017A
6391:Substance P
6376:GSK1702934A
6325:PF-04745637
6264:Umbellulone
6185:Pacific yew
6171:Oleocanthal
6150:wintergreen
6111:Ligustilide
5974:Cannabidiol
5939:horseradish
5176:2434/421160
4305:(1): 63β9.
4299:Circulation
4078:(4): 23β8.
3128:Circulation
2300:Xenobiotica
1934:(1): 1β12.
1505:Vasculature
1323:epinephrine
1263:(SNP) (see
1139:vasopressin
930:vasopressin
904:neutrophils
797:to form 12(
711:with human
677:lauric acid
652:gemfibrozil
610:endothelins
582:epoxygenase
340:Properties
146:CHEBI:34306
7673:Categories
7521:Cannabinol
7421:pooissonii
7412:Tinyatoxin
7363:pooissonii
7327:Probenecid
7317:Polygodial
7273:Paclitaxel
7257:PAVA spray
7144:Evodiamine
7095:pepperwort
7010:Anandamide
6977:Ξ±-Sanshool
6925:Activators
6878:Triptolide
6871:Activators
6783:Activators
6759:TRPM4-IN-5
6677:Elismetrep
6605:stevioside
6533:eucalyptus
6529:Eucalyptol
6493:ADP-ribose
6486:Activators
6422:GSK417651A
6381:Hyperforin
6354:Activators
6234:Tear gases
6206:Polygodial
6196:PF-4840154
6181:Paclitaxel
6049:Dicentrine
5959:Bradykinin
5894:Ξ±-Sanshool
5862:Activators
5844:modulators
5607:: 243β55.
4887:2020-05-24
4669:2018-08-27
2789:2019-08-16
2612:: 413β38.
1558:: 413β38.
1533:References
1430:Pseudogene
1411:MDA-MB-231
1246:Odds ratio
1167:transgenic
1048:Thrombosis
1044:thrombosis
934:endothelin
757:and to 11(
723:Metabolism
632:superoxide
588:products.
428:eicosanoid
375:Molar mass
178:IUPHAR/BPS
157:ChemSpider
113:3D model (
102:79551-86-3
92:CAS Number
7652:See also:
7636:TRPV3-74a
7621:SB-705498
7616:SB-366791
7566:Lanthanum
7561:HC-067047
7481:Asivatrep
7342:Rutamarin
7206:Incensole
7156:Gingerols
7125:Estradiol
7101:, others)
7083:Carvacrol
7073:Capsaicin
6967:13-oxoODE
6957:12S-HpETE
6937:5',6'-EET
6737:Rutamarin
6636:Thio-BCTC
6589:Rutamarin
6519:Coolact P
6310:HC-030031
6175:olive oil
6071:Gingerols
5884:12S-HpETE
4700:CiteSeerX
4307:CiteSeerX
1419:apoptosis
1361:orthologs
1257:haplotype
946:Androgens
835:chirality
739:platelets
598:Androgens
466:microsome
464:(CYP450)
7586:NGD-8243
7571:Mavatrep
7556:GRC-6211
7525:cannabis
7515:cannabis
7505:cannabis
7495:cannabis
7476:AMG-9810
7452:Blockers
7433:Vanillin
7428:Tramadol
7392:cannabis
7370:Shogaols
7303:Piperine
7067:cannabis
7057:cannabis
7035:rosemary
6952:12S-HETE
6947:9-oxoODE
6894:Blockers
6844:PI(4,5)P
6832:Blockers
6810:PI(3,5)P
6717:Ononetin
6702:Nicotine
6650:Blockers
6626:fructose
6618:tastants
6564:Linalool
6549:Geraniol
6509:CIM-0216
6400:Blockers
6315:Nicotine
6290:A-967079
6283:Blockers
6243:cannabis
6216:Shogaols
6161:Nicotine
6127:Linalool
6066:Formalin
6028:turmeric
6024:Curcumin
5998:cinnamon
5988:cannabis
5978:cannabis
5968:cannabis
5954:ASP-7663
5912:Acrolein
5798:19013235
5763:21503433
5755:16081682
5711:15059886
5676:37734580
5668:16243809
5633:23569388
5582:19846914
5541:21120482
5492:22798501
5448:11952881
5440:25701119
5402:21209903
5362:PLOS ONE
5343:25549350
5303:PLOS ONE
5284:25094029
5237:23747687
5193:19189811
5185:24337409
5139:13728834
5131:25178427
5096:23176821
5044:29628049
5030:: 6β13.
5008:34470511
5000:24418943
4964:19097922
4929:18787519
4878:Archived
4866:24984178
4824:18971550
4780:14217802
4772:21625857
4724:18574070
4663:Archived
4651:22173545
4612:17341693
4577:20130494
4525:18936345
4484:16144986
4443:23680415
4435:18300855
4380:18385420
4331:15611369
4245:22389490
4194:16691295
4137:20943934
4102:19713718
4053:11320253
3994:23641057
3904:19211690
3855:30640395
3812:23438293
3763:23220478
3714:21474427
3665:25820395
3630:23658377
3581:26569858
3573:24298905
3527:21610722
3473:27492226
3416:15226275
3381:15130884
3304:21239640
3233:14612451
3192:10841040
3148:15262846
3072:18391101
3026:10722687
2936:16081420
2841:25249502
2783:Archived
2779:24406470
2738:16835590
2661:20869469
2626:15822183
2591:23362865
2542:25427230
2480:16258232
2434:25526688
2386:21722750
2330:20021200
2281:25986599
2257:: 40β9.
2225:16527260
2173:20716162
2135:25872594
2099:20630735
2064:22841774
1996:22706230
1958:23584425
1902:23688133
1842:25813407
1818:: 9β16.
1745:18156192
1721:Falck JR
1703:18433732
1665:14660610
1621:20941528
1572:15822183
1511:receptor
1259:tagging
1165:Cyp4a12-
995:receptor
660:propanol
7606:RN-9893
7601:RN-1734
7471:AMG-517
7437:vanilla
7406:oregano
7378:Sichuan
7356:(RTX) (
7332:Protons
7295:(e.g.,
7228:Menthol
7210:incense
7130:Eugenol
7087:oregano
7027:Camphor
6995:Allicin
6985:Sichuan
6972:20-HETE
6962:13-HODE
6805:ML2-SA1
6706:tobacco
6657:AMG-333
6630:sucrose
6622:glucose
6620:(e.g.,
6603:(e.g.,
6569:Menthol
6503:Calcium
6319:tobacco
6295:AM-0902
6224:Sichuan
6165:tobacco
6054:Lindera
5931:mustard
5917:Allicin
5902:Sichuan
5879:4,5-EET
5841:channel
5719:5252711
5624:3615879
5573:2807614
5532:3839420
5483:3601443
5393:3012715
5370:Bibcode
5334:4280215
5311:Bibcode
5264:Bibcode
5217:Bibcode
5087:3516610
4874:6754178
4732:6884532
4659:7528853
4568:3932492
4371:2488260
4280:8274222
4236:3340178
4185:1459070
4093:2790762
4021:Bibcode
3985:3736709
3945:9039121
3895:2670635
3847:8258666
3803:4106241
3754:3567350
3705:3119152
3621:3684845
3518:3208155
3464:5091366
3345:1648091
3269:1525186
3156:9244739
3113:2501294
2985:7690778
2890:1327375
2881:1907511
2832:4617135
2697:9675028
2582:3791982
2533:4260681
2488:4694718
2425:4385421
2377:3248593
2321:3067055
2272:4575609
2205:Bibcode
2181:3481077
2055:3439529
2034:Bibcode
2004:5258044
1949:4292790
1893:4245146
1833:4575602
1780:9866708
1612:2962793
1265:Tag SNP
1093:nephron
1040:C57BL/6
1038:In the
697:12-HETE
648:opioids
586:epoxide
550:CYP4A22
533:CYP4A11
441:rodents
380:320.473
247:5283157
234:PubChem
166:4446281
7546:DHEA-S
7398:Thymol
7374:ginger
7297:4Ξ±-PDD
7160:ginger
6999:garlic
6981:ginger
6942:9-HODE
6839:ML-SI3
6800:ML-SA1
6795:MK6-83
6616:Sweet
6579:PMD 38
6559:Icilin
6412:DHEA-S
6304:celery
6220:ginger
6115:celery
6106:JT-010
6096:Icilin
6075:ginger
6038:celery
5943:wasabi
5935:radish
5921:garlic
5898:ginger
5796:
5761:
5753:
5717:
5709:
5674:
5666:
5631:
5621:
5580:
5570:
5539:
5529:
5490:
5480:
5446:
5438:
5400:
5390:
5341:
5331:
5282:
5235:
5191:
5183:
5137:
5129:
5094:
5084:
5042:
5006:
4998:
4962:
4927:
4872:
4864:
4822:
4778:
4770:
4730:
4722:
4702:
4657:
4649:
4610:
4575:
4565:
4523:
4482:
4441:
4433:
4378:
4368:
4329:
4309:
4278:
4243:
4233:
4192:
4182:
4145:959890
4143:
4135:
4100:
4090:
4051:
4041:
3992:
3982:
3943:
3902:
3892:
3853:
3845:
3810:
3800:
3761:
3751:
3712:
3702:
3663:
3628:
3618:
3579:
3571:
3525:
3515:
3471:
3461:
3424:434047
3422:
3414:
3379:
3343:
3302:
3267:
3231:
3190:
3154:
3146:
3111:
3070:
3024:
2983:
2976:288277
2973:
2934:
2888:
2878:
2839:
2829:
2777:
2736:
2695:
2659:
2624:
2589:
2579:
2540:
2530:
2486:
2478:
2432:
2422:
2384:
2374:
2328:
2318:
2279:
2269:
2223:
2179:
2171:
2133:
2097:
2062:
2052:
2002:
1994:
1956:
1946:
1900:
1890:
1840:
1830:
1778:
1743:
1701:
1663:
1619:
1609:
1570:
1459:Glioma
1403:Balb/c
1387:BT-474
1372:Cancer
1345:CYP4F2
1334:intron
1027:intima
689:5-HETE
630:, and
612:, and
578:CYP2J2
554:CYP2U1
546:CYP4Z1
541:CYP4F3
539:, and
537:CYP4F2
503:CYP4F8
499:CYP2U1
324:SMILES
208:C14748
44:Names
7536:DCDPC
7402:thyme
7138:clove
7134:basil
7091:thyme
7005:AM404
6932:2-APB
6818:SF-22
6790:EVP21
6774:TRPML
6672:DCDPC
6641:WS-12
6407:DCDPC
6258:onion
6135:thyme
6057:spp.)
6018:cumin
5949:AM404
5759:S2CID
5715:S2CID
5672:S2CID
5444:S2CID
5189:S2CID
5135:S2CID
5004:S2CID
4881:(PDF)
4870:S2CID
4842:(PDF)
4776:S2CID
4728:S2CID
4655:S2CID
4439:S2CID
4141:S2CID
4044:33189
3851:S2CID
3577:S2CID
3420:S2CID
3152:S2CID
2484:S2CID
2177:S2CID
2000:S2CID
1472:769-P
1468:786-O
1434:miRNA
1415:MCF-7
1207:TRPV1
1195:PPARΞ±
664:COX-2
656:Lasix
558:MCF-7
516:, 19(
295:InChI
137:ChEBI
115:JSmol
7541:DHEA
7486:BCTC
7380:and
7337:RhTx
7232:mint
7220:Low
7171:Heat
7105:DHEA
6987:and
6916:TRPV
6862:TRPP
6823:SN-2
6754:TPPO
6573:mint
6514:Cold
6498:BCTC
6477:TRPM
6457:Pyr3
6345:TRPC
6226:and
5904:and
5853:TRPA
5794:PMID
5751:PMID
5707:PMID
5664:PMID
5629:PMID
5578:PMID
5537:PMID
5488:PMID
5436:PMID
5398:PMID
5339:PMID
5280:PMID
5233:PMID
5181:PMID
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