286:
191:
6500:
27:
5772:
415:
500:)-Equol was first isolated from horse urine in 1932, and the name was suggested by this equine connection. Since then, equol has been found in the urine or plasma of many other animal species, although these animals have significant differences in their ability to metabolize daidzein into equol. In 1980, scientists reported the discovery of equol in humans. The ability of (
2501:
Effect of natural S-equol on bone metabolism in equol non-producing postmenopausal
Japanese women: a pilot randomized placebo-controlled trial. Tomomi Ueno of Saga Nutraceutricals Research Institute, Otsuka Pharmaceutical Co., Ltd., Japan,
1097:
Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). "Equol, a natural estrogenic metabolite from soy isoflavones".
924:
of both enantiomers have different characteristics, bioavailabilities and molecular effects. According to one study, (RS)-equol provided the greatest overall improvement in skin health, especially when applied topically.
909:. Equol's phytoestrogenic properties may also affect skin health. Reduction of dark circles and eye wrinkles after treatment with equol has been reported. Equol may also protect skin from damage by pollution due to its
1837:
Rowland, IR; Wiseman, H; Sanders, TA; Adlercreutz, H; Bowey, EA (2000). "Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora".
2292:
Reeve V, Widyarini S, Domanski D, Chew K, Barnes K. Protection
Against Photoaging in the Hairless Mouse by the Isoflavone Equol. Photochemistry and Photobiology, Volume 81, Issue 6, November 2005, Pages
713:)-equol after eating soy foods containing isoflavones, while 50 to 60 percent of adults from Japan, Korea, and China are equol-producers. Vegetarians have also been reported to be more capable of transforming
2303:
Magnet, U.; Urbanek, C.; Gaisberger, D.; Tomeva, E.; Dum, E.; Pointner, A.; Haslberger, A.G. (October 2017). "Topical equol preparation improves structural and molecular skin parameters".
2390:
Urbanek C, Haslberger A, Hippe B, Gessner D, Fiala H, Equol – a
Topically Applied Phyto-Oestrogen Improves Skin Characteristics. Global ingredients and Formulations Guide 2016
2267:
689:)-equol in urine after oral administration is high and in some adults can reach close to 100 percent. The percent fractional elimination of daidzein is much lower at 30 to 40 percent.
3337:
3332:
1614:"The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers"
681:
form (without the glucose side chain) via removal of the sugar side chain during digestion before it can use daidzein. If consumed directly in aglycone form, daidzein has a T
2402:"Equol's Anti-Aging Effects Protect against Environmental Assaults by Increasing Skin Antioxidant Defense and ECM Proteins While Decreasing Oxidative Stress and Inflammation"
5218:
2446:"Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin"
893:
substance have been shown in different studies. The effects result from both molecular and structural changes to the skin. Equol can, for instance, lead to an increase in
1965:"Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents"
2178:"S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora"
1514:"S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora"
1337:
Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). "Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease".
5450:
4790:
2869:
2700:
729:
for at least a month. For this standardized test, the individual drinks two 240 milliliter glasses of soy milk or eats a soy food equivalent for three days. The (
6297:
1512:
Setchell, KD; Clerici, C; Lephart, ED; Cole, SJ; Heenan, C; Castellani, D; Wolfe, BE; Nechemias-Zimmer, L; Brown, NM; Lund, TD; Handa, RJ; Heubi, JE (May 2005).
2492:
Efficacy and safety of natural S-equol supplement in US postmenopausal women. Belinda H. Jenks of
Scientific Affairs, Pharmavite LLC, Northridge, CA, et.al.
3269:
2554:"Equol Is a Novel Anti-Androgen that Inhibits Prostate Growth and Hormone Feedback, Biology of Reproduction, Volume 70, Issue 4, 1 April 2004, Pages 1188–1195"
941:, such as vaginal itching, vaginal dryness and pain with intercourse and cause positive shifts in the vaginal bacterial population, cell composition, and pH.
2695:
2690:
1428:
Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). "Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health".
2969:
1473:"Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor {α} (ER{α}) and ERβ in human cells"
709:)-equol or a related intermediate compound. Several studies indicate that only 25 to 30 percent of the adult populations of Western countries produce (
6292:
6219:
428:
5365:
5131:
3322:
5655:
5182:
5174:
2176:
Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE (2005).
649:)-Equol is a very stable molecule that essentially remains unchanged when digested, and this lack of further metabolism explains its very quick
4757:
121:
5650:
5517:
5512:
5010:
5005:
5000:
4870:
741:
While many more bacteria are involved in the related intermediate process of equol production, such as conversion of daidzin to daidzein, or
701:)-equol after soy consumption, humans must have certain strains of bacteria living within their intestines. Twenty-one different strains of
1963:
Akaza, H; Miyanaga, N; Takashima, N; Naito, S; Hirao, Y; Tsukamoto, T; Fujioka, T; Mori, M; Kim, WJ; Song, JM; Pantuck, AJ (February 2004).
1924:"Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake"
6538:
5476:
5396:
5193:
4495:
4279:
335:
3982:
128:
5268:
5263:
5035:
4960:
1753:
Lampe, JW; Karr, SC; Hutchins, AM; Slavin, JL (March 1998). "Urinary equol excretion with a soy challenge: influence of habitual diet".
6224:
5243:
5238:
5085:
5080:
3432:
3262:
2705:
1618:
1518:
1339:
5578:
5411:
5406:
5090:
4925:
4880:
4229:
2514:"Eine Proof-of-concept-Studie von Isoflavandiol-E55-RS-Vaginalkapseln oder Vaginalgel zur Linderung der menopausalen Vaginalatrophie"
2346:
Lephart ED (November 2016). "Skin aging and oxidative stress: Equol's anti-aging effects via biochemical and molecular mechanisms".
5248:
5156:
5151:
5141:
5055:
4980:
3992:
937:
symptoms such as hot flashes and muscle and joint pain. (RS)-equol was also reported to reduce symptoms associated with menopausal
5095:
2590:
1883:"Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako)"
505:
4771:
625:)-equol to ERβ vs. ERα and in comparison to that of estradiol suggests the molecule may share some of the characteristics of a
5616:
5573:
3255:
2277:
626:
5568:
4064:
3542:
1881:
Watanabe, S; Yamaguchi, M; Sobue, T; Takahashi, T; Miura, T; Arai, Y; Mazur, W; Wähälä, K; Adlercreutz, H (October 1998).
5302:
3527:
3522:
6543:
3575:
3100:
1037:"Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium"
300:
3591:
3085:
4146:
3712:
435:
4726:
3090:
423:
3786:
3754:
6135:
3977:
1287:"The identification of the weak oestrogen equol [7-hydroxy-3-(4'-hydroxyphenyl)chroman] in human urine"
844:
Conversion by
Bifidobacterium has only been reported once by Tsangalis et al. in 2002 and not reproduced since.
2006:"Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls"
5688:
536:)-equol is produced in humans and animals with the ability to metabolize the soy isoflavone daidzein, while (
53:
5563:
3877:
873:
509:
243:
186:
5327:
3437:
3412:
309:
InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1
5583:
3825:
2583:
319:
InChI=1/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1
264:
148:
1384:"The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones"
901:(ROS). It may also act as a protective anti-photoaging substance by inhibiting acute UVA- induced lipid
5919:
3830:
6472:
5609:
4885:
4795:
4017:
833:
666:
650:
5751:
5446:
5208:
5121:
4746:
4439:
3972:
3967:
3867:
3150:
3065:
1665:"The pharmacokinetics of S-(-)equol administered as SE5-OH tablets to healthy postmenopausal women"
773:
281:
6533:
6528:
6466:
5788:
4734:
4644:
4269:
4259:
4194:
3722:
3492:
3175:
3145:
2348:
1143:"High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart"
898:
758:
614:
3532:
3507:
3447:
3442:
2553:
2096:"Dietary seaweed modifies estrogen and phytoestrogen metabolism in healthy postmenopausal women"
2004:
Song, KB; Atkinson, C; Frankenfeld, CL; Jokela, T; Wähälä, K; Thomas, WK; Lampe, JW (May 2006).
1015:
6523:
6429:
4702:
4254:
3734:
3659:
3654:
3607:
2576:
1922:
Arai, Y; Uehara, M; Sato, Y; Kimira, M; Eboshida, A; Adlercreutz, H; Watanabe, S (March 2000).
890:
721:
and dairy consumption can enhance the production of equol. The ability of a person to produce (
618:
553:
3462:
1016:
Structural
Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MS
861:
845:
6196:
4975:
4800:
4738:
4264:
3808:
3771:
3759:
3627:
3160:
897:
length. As an antioxidant, equol can decrease the aging process by reducing damage caused by
869:
828:
803:
39:
3537:
3512:
3487:
3472:
3407:
3347:
3342:
1472:
1184:"Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares' urine"
6029:
5602:
4395:
4052:
3791:
3697:
3639:
3417:
2662:
1048:
813:
788:
252:
168:
3477:
3352:
3327:
8:
6357:
6234:
6055:
5456:
5371:
4435:
4219:
4076:
4042:
3852:
3552:
996:
949:
285:
190:
97:
87:
3467:
1052:
6247:
5934:
5538:
5322:
5203:
4785:
4399:
4059:
3717:
3634:
3579:
3422:
3382:
3372:
3312:
3281:
2685:
2373:
2328:
2243:
2218:
2071:
2046:
1863:
1778:
1730:
1705:
1640:
1613:
1589:
1556:
1453:
1364:
1311:
1286:
1262:
1237:
1208:
1183:
938:
5126:
3402:
1069:
1036:
944:
According to animal studies, it has anti-androgenic effects and may lead to inhibited
6504:
6477:
6414:
6409:
6284:
6274:
5681:
5136:
4910:
4359:
3367:
3362:
3289:
3278:
3155:
2535:
2475:
2467:
2423:
2377:
2365:
2320:
2273:
2248:
2199:
2158:
2117:
2076:
2027:
1986:
1945:
1904:
1855:
1819:
1770:
1735:
1686:
1645:
1594:
1576:
1537:
1494:
1445:
1405:
1356:
1316:
1285:
Axelson, M; Kirk, DN; Farrant, RD; Cooley, G; Lawson, AM; Setchell, KD (1982-02-01).
1267:
1213:
1164:
1123:
1115:
1074:
966:
945:
914:
778:
705:
cultured from humans have been shown to have the ability to transform daidzein into (
3517:
2332:
1867:
1782:
1457:
6024:
5386:
4855:
3820:
3567:
3452:
3392:
3387:
3377:
3357:
3317:
3006:
2677:
2525:
2457:
2413:
2357:
2312:
2238:
2230:
2189:
2148:
2107:
2066:
2058:
2017:
1976:
1935:
1894:
1847:
1809:
1762:
1725:
1717:
1676:
1635:
1627:
1584:
1568:
1527:
1484:
1437:
1395:
1368:
1348:
1306:
1298:
1257:
1249:
1203:
1195:
1154:
1107:
1064:
1056:
363:
3497:
1060:
232:
6486:
5977:
4945:
4678:
4552:
4184:
4131:
4086:
3887:
3185:
2954:
2814:
2462:
2445:
921:
768:
654:
6110:
4656:
4652:
4630:
3016:
3011:
2062:
6328:
6152:
5858:
5848:
5416:
5178:
5050:
4479:
4199:
4171:
4163:
4002:
3907:
3897:
3842:
3837:
3739:
3557:
3457:
3247:
3170:
2907:
2629:
2607:
1766:
1441:
976:
702:
540:-equol can be chemically synthesized. The molecular and physical structure of (
406:
5982:
2530:
2513:
2361:
2137:"Method of defining equol-producer status and its frequency among vegetarians"
1851:
1798:"Method of defining equol-producer status and its frequency among vegetarians"
1572:
1557:"Estrogen biology: New insights into GPER function and clinical opportunities"
1111:
733:)-equol concentration in each test subject's urine is determined on day four.
6517:
6449:
6384:
5939:
5901:
5798:
5030:
4865:
4840:
4620:
4538:
4371:
4349:
4204:
4081:
3813:
3664:
3622:
3032:
2920:
2897:
2874:
2539:
2471:
2427:
2418:
2401:
2194:
2177:
1899:
1882:
1580:
1532:
1513:
1400:
1383:
1119:
865:
849:
808:
753:
451:
179:
2153:
2136:
2022:
2005:
1814:
1797:
1631:
1489:
1352:
6481:
6424:
6419:
6399:
6345:
6317:
6313:
6269:
6264:
5891:
5863:
5756:
5731:
5674:
5198:
5170:
5146:
5015:
4940:
4850:
4845:
4835:
4638:
4604:
4594:
4590:
4525:
4519:
4451:
3947:
3937:
3912:
3776:
3729:
3583:
3571:
3130:
2983:
2773:
2738:
2599:
2479:
2369:
2324:
2252:
2203:
2162:
2121:
2080:
2031:
1990:
1949:
1859:
1823:
1739:
1690:
1649:
1598:
1541:
1498:
1449:
1409:
1271:
1217:
1168:
1127:
1078:
902:
818:
574:
482:
2234:
2112:
2095:
1981:
1964:
1908:
1836:
1774:
1721:
1681:
1664:
1360:
1320:
1253:
1014:
The structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in
6394:
6125:
6014:
5853:
5813:
5761:
5741:
5716:
5543:
5471:
5436:
5431:
5391:
5361:
5347:
5337:
5332:
5161:
5105:
5100:
4995:
4990:
4970:
4920:
4895:
4890:
4815:
4805:
4722:
4718:
4714:
4706:
4696:
4692:
4660:
4648:
4634:
4626:
4566:
4499:
4443:
4415:
4249:
4224:
4096:
3997:
3872:
3796:
3766:
3617:
3597:
3547:
3501:
3397:
3135:
3115:
3080:
3075:
3070:
3055:
2996:
2991:
2964:
2837:
2783:
2723:
2715:
2639:
910:
906:
853:
838:
793:
783:
763:
1880:
1159:
1142:
677:(with a glucose side chain) form. The body must convert daidzein to its
488:. Only about 30–50% of people have intestinal bacteria that make equol.
6333:
6105:
6034:
5886:
5873:
5838:
5721:
5631:
5486:
5466:
5441:
5288:
5233:
5188:
5166:
5075:
5070:
5040:
5025:
5020:
4985:
4875:
4830:
4810:
4688:
4682:
4586:
4574:
4534:
4515:
4491:
4475:
4385:
4381:
4355:
4341:
4294:
4289:
4284:
4274:
4244:
4214:
4209:
4189:
4126:
4047:
4027:
4012:
4007:
3952:
3902:
3803:
3744:
3677:
3672:
3649:
3587:
3562:
3165:
3120:
3110:
3105:
2959:
2892:
2864:
2851:
2634:
2624:
2616:
2003:
1940:
1923:
991:
986:
798:
726:
521:
470:
462:
391:
159:
3987:
3482:
2316:
1302:
1199:
520:
Equol is a compound that can exist in two mirror-image forms known as
6170:
6160:
6130:
5958:
5909:
5843:
5833:
5828:
5823:
5736:
5645:
5481:
5461:
5401:
5381:
5223:
5060:
4935:
4930:
4915:
4900:
4860:
4742:
4710:
4668:
4616:
4612:
4608:
4598:
4578:
4562:
4511:
4487:
4483:
4471:
4463:
4459:
4419:
4407:
4391:
4377:
4367:
4363:
4319:
4179:
4153:
4141:
4116:
4106:
4091:
4071:
4022:
3922:
3917:
3892:
3882:
3847:
3707:
3682:
3644:
3602:
2938:
2859:
2827:
2822:
2804:
2753:
2743:
2667:
1511:
1336:
971:
934:
864:
Some equol producing bacteria, as implied by their nomenclature, are
742:
674:
610:
545:
474:
5666:
3427:
1962:
1141:
Frankenfeld CL, Atkinson C, Thomas WK, et al. (December 2005).
405:
Except where otherwise noted, data are given for materials in their
6404:
6362:
6350:
6185:
6175:
6165:
6120:
6095:
6009:
5987:
5929:
5881:
5793:
5352:
5342:
5045:
4905:
4825:
4820:
4753:
4570:
4507:
4503:
4467:
4455:
4427:
4423:
4411:
4403:
4333:
4121:
4111:
3957:
3942:
3927:
3862:
3857:
3702:
3612:
3208:
3095:
3060:
2930:
2843:
2768:
2763:
2748:
2728:
2657:
2649:
1752:
1284:
961:
894:
714:
678:
485:
466:
458:
454:
207:
6075:
1662:
1381:
933:
Beyond topical effects, medicinal equol has been shown to relieve
127:
120:
26:
6439:
6434:
6338:
6323:
6202:
6115:
5967:
5818:
5746:
5726:
5697:
5507:
5253:
5065:
4965:
4955:
4950:
4730:
4674:
4664:
4556:
4431:
4239:
4234:
4136:
4101:
4032:
3932:
3781:
3749:
3687:
3140:
3125:
3001:
2915:
2884:
2795:
2733:
981:
823:
718:
630:
578:
478:
219:
2568:
1755:
Proceedings of the
Society for Experimental Biology and Medicine
1612:
Setchell, KD; Zhao, X; Jha, P; Heubi, JE; Brown, NM (Oct 2009).
1471:
Mueller SO, Simon S, Chae K, Metzler M, Korach KS (April 2004).
1427:
6444:
6238:
6180:
6065:
6060:
6050:
5914:
5808:
5803:
5771:
5426:
5421:
5278:
4542:
4530:
4345:
4314:
4309:
4304:
4037:
3692:
3218:
3213:
2758:
1018:
by
Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in
725:)-equol is determined by testing people who have not taken any
139:
5594:
4772:
1611:
685:
of one to three hours. The percent fractional elimination of (
590:
582:
6389:
6100:
6070:
5972:
5502:
5258:
5228:
4329:
4158:
2512:
Mayr, Linda; Georgiev, Dimitar; Toulev, Albena (2019-03-01).
2302:
1921:
110:
1382:
Setchell, KD; Brown, NM; Lydeking-Olsen, E (December 2002).
661:)-equol is consumed, it is rapidly absorbed and achieves a T
269:
6019:
5924:
5522:
5303:
5213:
4582:
4337:
634:
198:
2175:
5357:
1663:
Setchell, KD; Zhao, X; Shoaf, SE; Ragland, K (Nov 2009).
1140:
1035:
Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005).
673:
of daidzein is 4 to 10 hours because daidzein exists in
617:(ERα) and 20% of estradiol's binding affinity for human
1470:
1096:
3673:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
2269:
Beneficial
Microbes in Fermented and Functional Foods
2518:
2439:
2437:
1181:
905:. In addition, equol may have a positive impact on
1548:
469:and other plant sources, by bacterial flora in the
2511:
1703:
1235:
745:to 5-Hydroxy-equol, the bacteria that achieve the
512:diseases or disorders was first proposed in 1984.
6489:, artisan town of historic soy sauce distilleries
2434:
2266:V, Ravishankar Rai; Bai, Jamuna A. (2014-12-17).
2044:
928:
6515:
3277:
2134:
1795:
1706:"Equol: pharmacokinetics and biological actions"
1092:
1090:
1088:
231:
16:Isoflavandiol estrogen metabolized from daidzein
2216:
1554:
1423:
1421:
1419:
589:= 16 nM) with 13-fold selectivity for ERβ over
473:. While endogenous estrogenic hormones such as
96:
4777:Tooltip Selective estrogen receptor modulators
4132:Furostilbestrol (diethylstilbestrol difuroate)
3493:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
2093:
862:Bifidobacteria: Genomics and Molecular Aspects
846:Bifidobacteria: Genomics and Molecular Aspects
605:= 50 nM) with 3.5-fold selectivity over ERβ. (
5682:
5610:
3323:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3263:
2584:
1555:Prossnitz, Eric R.; Barton, Matthias (2014).
1332:
1330:
1085:
1034:
669:) in two to three hours. In comparison, the T
3433:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
2339:
2169:
1416:
564:
5308:Tooltip G protein-coupled estrogen receptor
4127:Fosfestrol (diethylstilbestrol diphosphate)
2045:Patisaul, HB; Jefferson, W (October 2010).
736:
504:)-equol to play a role in the treatment of
5689:
5675:
5617:
5603:
4270:Triphenylmethylethylene (triphenylpropene)
3594:, many others; via estrogenic metabolites)
3518:17α-Epiestriol (16α-hydroxy-17α-estradiol)
3270:
3256:
3025:
2591:
2577:
2219:"Equol: History, Chemistry, and Formation"
1619:The American Journal of Clinical Nutrition
1519:The American Journal of Clinical Nutrition
1340:The American Journal of Clinical Nutrition
1327:
1238:"Equol: history, chemistry, and formation"
1231:
1229:
1227:
1030:
1028:
629:(SERM). Equol has been found to act as an
601:)-equol is less potent and binds to ERα (K
544:)-equol is similar to that of the hormone
284:
189:
167:
3290:
2529:
2461:
2417:
2305:International Journal of Cosmetic Science
2242:
2193:
2152:
2111:
2070:
2021:
1980:
1939:
1898:
1813:
1729:
1680:
1639:
1588:
1531:
1488:
1464:
1399:
1310:
1261:
1207:
1158:
1068:
251:
1008:
2443:
2399:
2345:
1224:
1025:
692:
280:
6516:
2135:Setchell, KD; Cole, SJ (August 2006).
1796:Setchell, KD; Cole, SJ (August 2006).
1236:Setchell, KD; Clerici, C (July 2010).
1134:
180:
5696:
5670:
5598:
3251:
2572:
2217:Setchell, K. D.; Clerici, C. (2010).
2047:"The pros and cons of phytoestrogens"
1969:Japanese Journal of Clinical Oncology
1704:Setchell, KD; Clerici, C (Jul 2010).
627:selective estrogen receptor modulator
515:
312:Key: ADFCQWZHKCXPAJ-GFCCVEGCSA-N
147:
2265:
2094:Teas, J.; Hurley, TG (August 2009).
1561:Molecular and Cellular Endocrinology
1100:Bioorganic & Medicinal Chemistry
621:(ERβ). The preferential binding of (
343:C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
6539:Steroid sulfotransferase inhibitors
2444:Lephart, Edwin D. (November 2013).
1182:Marrian, GF; Haslewood, GA (1932).
889:The topical effects of equol as an
749:of daidzein to (S)-equol, include:
640:
322:Key: ADFCQWZHKCXPAJ-GFCCVEGCBP
222:
206:
62:)-3-(4-Hydroxyphenyl)-3,4-dihydro-2
13:
829:Slackia equolifaciens (Strain DZE)
14:
6555:
4669:taleranol (teranol, β-zearalanol)
3584:metandienone (methandrostenolone)
2598:
1430:Experimental Biology and Medicine
879:
856:sp. Julong 732 can also produce (
6499:
6498:
5770:
5579:Progesterone receptor modulators
5333:Afimoxifene (4-hydroxytamoxifen)
4215:Prinaberel (ERB-041, WAY-202041)
920:Each of the enantiomers and the
413:
375:
25:
5624:
5276:Coregulator-binding modulators:
3543:17β-Methyl-17α-dihydroequilenin
2546:
2505:
2495:
2486:
2393:
2384:
2296:
2286:
2259:
2210:
2128:
2087:
2038:
1997:
1956:
1915:
1874:
1830:
1789:
1746:
1697:
1656:
1605:
1505:
1022:(2005, electronic publication).
1020:Drug Metabolism and Disposition
814:Lactococcus garvieae (Lc 20-92)
759:Asaccharobacter celatus AHU1763
559:
409:(at 25 °C , 100 kPa).
6136:List of fermented soy products
4107:Erteberel (SERBA-1, LY-500307)
1375:
1278:
1175:
929:Hormone-related health effects
884:
613:'s binding affinity for human
381:
369:
1:
6111:Soy milk based infant formula
5564:Receptor/signaling modulators
3528:17α-Ethynyl-3β-androstanediol
3523:17α-Ethynyl-3α-androstanediol
2400:Lephart, Edwin (2018-01-29).
1061:10.1128/AEM.71.1.214-219.2005
1002:
552:)-Equol preferentially binds
348:Oc1ccc(cc1)2Cc3c(OC2)cc(O)cc3
5574:Androgen receptor modulators
3878:Lynestrenol phenylpropionate
2463:10.3109/13880209.2013.793720
874:Slackia isoflavoniconvertens
7:
5569:Estrogens and antiestrogens
5219:Oxabicycloheptene sulfonate
4906:Etacstil (GW-5638, DPC-974)
4082:Doisynoestrol (fenocycline)
3826:Ethinylestradiol 3-benzoate
3338:3β,5α-Dihydrolevonorgestrel
3333:3α,5α-Dihydrolevonorgestrel
2063:10.1016/j.yfrne.2010.03.003
955:
754:Adlercreutzia equolifaciens
450:(4',7-isoflavandiol) is an
10:
6560:
5920:Textured vegetable protein
5286:Noncompetitive inhibitors:
4911:Ethamoxytriphetol (MER-25)
4072:Dimestrol (dianisylhexene)
3831:Ethinylestradiol sulfonate
1767:10.3181/00379727-217-44241
1442:10.1177/153537020523000302
779:Coriobacteriaceae sp MT1B9
491:
6496:
6473:Kikkoman Soy Sauce Museum
6458:
6377:
6306:
6283:
6257:
6233:
6212:
6151:
6144:
6088:
6043:
6002:
5957:
5948:
5900:
5872:
5779:
5768:
5709:
5630:
5556:
5531:
5495:
5328:7β-Hydroxyepiandrosterone
5315:
5301:
5114:
4886:Desmethylchlorotrianisene
4767:
4065:Diethylstilbestrol esters
4018:Bisdehydrodoisynolic acid
3438:11β-Chloromethylestradiol
3413:7β-Hydroxyepiandrosterone
3302:
3295:Tooltip Estrogen receptor
3288:
3184:
3048:
2982:
2947:
2929:
2906:
2883:
2850:
2836:
2813:
2782:
2714:
2676:
2648:
2615:
2606:
2531:10.1007/s41974-019-0085-9
2362:10.1016/j.arr.2016.08.001
1852:10.1207/S15327914NC3601_5
1573:10.1016/j.mce.2014.02.002
1112:10.1016/j.bmc.2003.11.035
950:dihydrotestosterone (DHT)
834:Streptococcus intermedius
667:peak plasma concentration
565:Estrogen receptor binding
403:
356:
331:
296:
80:
72:
52:
38:
33:
24:
5392:Fulvestrant (ICI-182780)
5209:Methylpiperidinopyrazole
5162:Fulvestrant (ICI-182780)
4645:Resorcylic acid lactones
3868:Hydroxyestrone diacetate
3804:Etamestrol (eptamestrol)
2419:10.3390/cosmetics5010016
2223:The Journal of Nutrition
2141:The Journal of Nutrition
2100:The Journal of Nutrition
2010:The Journal of Nutrition
1887:The Journal of Nutrition
1802:The Journal of Nutrition
1710:The Journal of Nutrition
1669:The Journal of Nutrition
1388:The Journal of Nutrition
1242:The Journal of Nutrition
1041:Appl. Environ. Microbiol
809:Lactobacillus sp Niu-O16
794:Eubacterium sp D1 and D2
774:Bifidobacterium animalis
737:Equol producing bacteria
609:)-Equol has about 2% of
6467:Diet for a Small Planet
5789:List of soy-based foods
4703:Synthetic xenoestrogens
4260:Triphenylchloroethylene
4195:Methestrol dipropionate
3723:Polyestradiol phosphate
3176:Perfluorinated compound
2349:Ageing Research Reviews
1928:Journal of Epidemiology
1632:10.3945/ajcn.2009.27981
1291:The Biochemical Journal
1188:The Biochemical Journal
899:reactive oxygen species
848:Mixed cultures such as
615:estrogen receptor alpha
6544:Selective ERβ agonists
4796:4'-Hydroxynorendoxifen
4791:2-Phenylbenzothiophene
4665:zeranol (α-zearalanol)
4368:phlorizin (phloridzin)
4255:Triphenylbromoethylene
4154:ICI-85966 (Stilbostat)
3735:Estramustine phosphate
3608:Bolandiol dipropionate
3002:α-Zearalanol (zeranol)
2870:Desmethylwedelolactone
2701:6,8-Diprenylnaringenin
2450:Pharmaceutical Biology
2195:10.1093/ajcn/81.5.1072
1900:10.1093/jn/128.10.1710
1533:10.1093/ajcn/81.5.1072
1401:10.1093/jn/132.12.3577
819:Ruminococcus productus
619:estrogen receptor beta
554:estrogen receptor beta
6298:Bowman-Birk inhibitor
4976:Miproxifene phosphate
4801:27-Hydroxycholesterol
4265:Triphenyliodoethylene
3809:Ethinylandrostenediol
3772:Estrogenic substances
3760:Polyestriol phosphate
3628:Cloxestradiol acetate
2235:10.3945/jn.109.119776
2154:10.1093/jn/136.8.2188
2113:10.3945/jn.108.100834
2051:Front Neuroendocrinol
2023:10.1093/jn/136.5.1347
1815:10.1093/jn/136.8.2188
1722:10.3945/jn.109.119784
1682:10.3945/jn.109.110874
1490:10.1093/toxsci/kfh147
1353:10.1093/ajcn/40.3.569
1254:10.3945/jn.109.119776
907:epigenetic regulation
870:Slackia equolifaciens
804:Lactobacillus mucosae
784:Eggerthella sp YY7918
54:Systematic IUPAC name
47:)-Isoflavan-4,7′-diol
6213:Globulins (proteins)
6030:Yellow soybean paste
4290:WAY-204688 (SIM-688)
4102:ERB-196 (WAY-202196)
4053:Dienestrol diacetate
3792:Estrone methyl ether
3698:Esterified estrogens
3640:Conjugated estrogens
3533:17β-Dihydroequilenin
3508:17α-Dihydroequilenin
3448:15α-Hydroxyestradiol
3443:11β-Methoxyestradiol
3418:8,9-Dehydroestradiol
2663:7,8-Dihydroxyflavone
1840:Nutrition and Cancer
789:Enterococcus faecium
693:Production in humans
6358:Protease Inhibitors
6056:Fermented bean curd
5457:Propylpyrazoletriol
5372:Diarylpropionitrile
4220:Propylpyrazoletriol
4077:Dimethylstilbestrol
4043:Diarylpropionitrile
3853:Etynodiol diacetate
3553:Abiraterone acetate
3463:16α-Fluoroestradiol
2696:8-Geranylnaringenin
1982:10.1093/jjco/hyh015
1160:10.1079/bjn20051565
1053:2005ApEnM..71..214W
997:Diarylpropionitrile
948:as well as lowered
747:complete conversion
703:intestinal bacteria
399: g·mol
21:
6505:Category: Soybeans
6285:Trypsin inhibitors
6275:Cysteine proteases
6248:Soybean agglutinin
5935:Vegetarian hot dog
5539:Diethylstilbestrol
5323:2-Methoxyestradiol
5254:TAS-108 (SR-16234)
5204:Methylepitiostanol
5142:EM-800 (SCH-57050)
5066:TAS-108 (SR-16234)
4786:2-Phenylbenzofuran
4400:8-prenylnaringenin
4060:Diethylstilbestrol
3718:Lipoidal estradiol
3693:ERA-63 (ORG-37663)
3635:Conjugated estriol
3580:methyltestosterone
3538:17β-Dihydroequilin
3513:17α-Dihydroequilin
3488:16β-Hydroxyestrone
3473:16α-Hydroxyestrone
3423:8,9-Dehydroestrone
3408:7α-Methylestradiol
3383:4-Methoxyestradiol
3373:4-Hydroxyestradiol
3348:3β-Hydroxytibolone
3343:3α-Hydroxytibolone
3313:2-Hydroxyestradiol
2691:6-Prenylnaringenin
2686:8-Prenylnaringenin
2229:(7): 1355S–1362S.
1941:10.2188/jea.10.127
764:Bacteroides ovatus
516:Chemical structure
436:Infobox references
75:4',7-Isoflavandiol
66:-1-benzopyran-7-ol
19:
6511:
6510:
6478:William Shurtleff
6410:Morningstar Farms
6373:
6372:
6084:
6083:
5664:
5663:
5592:
5591:
5584:List of estrogens
5552:
5551:
5297:
5296:
5137:Cytestrol acetate
4360:isoliquiritigenin
4302:Unknown/unsorted:
3988:β-LGND2 (GTx-878)
3568:Anabolic steroids
3478:16α-Iodoestradiol
3368:4-Fluoroestradiol
3363:4-Androstenedione
3353:3β-Androstanediol
3328:3α-Androstanediol
3279:Estrogen receptor
3245:
3244:
3156:Pentachlorophenol
3044:
3043:
3035:
2978:
2977:
2456:(11): 1393–1400.
2317:10.1111/ics.12408
2279:978-1-4822-0663-0
2182:Am. J. Clin. Nutr
1303:10.1042/bj2010353
1200:10.1042/bj0261227
967:Estrogen receptor
946:5-alpha reductase
915:anti-inflammatory
717:into (S)-equol.
510:androgen-mediated
457:metabolized from
444:Chemical compound
442:
441:
265:CompTox Dashboard
129:Interactive image
122:Interactive image
6551:
6502:
6501:
6293:Kunitz inhibitor
6220:Beta-conglycinin
6149:
6148:
6025:Sweet bean sauce
5955:
5954:
5774:
5691:
5684:
5677:
5668:
5667:
5619:
5612:
5605:
5596:
5595:
5451:2,2',5'-PCB-4-OH
5387:Ethinylestradiol
5313:
5312:
5309:
5305:
5046:Rimostil (P-081)
4856:Chlorotrianisene
4778:
4774:
4553:Metalloestrogens
4332:-related (e.g.,
4147:Hexestrol esters
3821:Ethinylestradiol
3713:Estradiol esters
3468:16α-Hydroxy-DHEA
3453:16-Ketoestradiol
3393:5-Androstenediol
3388:4-Methoxyestrone
3378:4-Hydroxyestrone
3358:4-Androstenediol
3318:2-Hydroxyestrone
3300:
3299:
3296:
3292:
3272:
3265:
3258:
3249:
3248:
3186:Metalloestrogens
3033:
3023:
3022:
2815:Dihydrochalcones
2678:Prenylflavonoids
2613:
2612:
2593:
2586:
2579:
2570:
2569:
2564:
2563:
2561:
2560:
2550:
2544:
2543:
2533:
2509:
2503:
2499:
2493:
2490:
2484:
2483:
2465:
2441:
2432:
2431:
2421:
2397:
2391:
2388:
2382:
2381:
2343:
2337:
2336:
2300:
2294:
2290:
2284:
2283:
2263:
2257:
2256:
2246:
2214:
2208:
2207:
2197:
2173:
2167:
2166:
2156:
2132:
2126:
2125:
2115:
2091:
2085:
2084:
2074:
2042:
2036:
2035:
2025:
2001:
1995:
1994:
1984:
1960:
1954:
1953:
1943:
1919:
1913:
1912:
1902:
1878:
1872:
1871:
1834:
1828:
1827:
1817:
1793:
1787:
1786:
1750:
1744:
1743:
1733:
1701:
1695:
1694:
1684:
1660:
1654:
1653:
1643:
1609:
1603:
1602:
1592:
1552:
1546:
1545:
1535:
1509:
1503:
1502:
1492:
1468:
1462:
1461:
1425:
1414:
1413:
1403:
1379:
1373:
1372:
1334:
1325:
1324:
1314:
1282:
1276:
1275:
1265:
1248:(7): 1355S–62S.
1233:
1222:
1221:
1211:
1179:
1173:
1172:
1162:
1138:
1132:
1131:
1106:(6): 1559–1567.
1094:
1083:
1082:
1072:
1032:
1023:
1012:
852:sp. Niu-O16 and
799:Finegoldia magna
641:Pharmacokinetics
426:
420:
417:
416:
398:
383:
377:
371:
364:Chemical formula
289:
288:
273:
271:
255:
235:
224:
210:
193:
182:
171:
151:
131:
124:
100:
29:
22:
18:
6559:
6558:
6554:
6553:
6552:
6550:
6549:
6548:
6514:
6513:
6512:
6507:
6492:
6454:
6369:
6329:Unsaponifiables
6302:
6279:
6253:
6229:
6208:
6140:
6080:
6039:
5998:
5978:Sweet soy sauce
5950:
5944:
5896:
5868:
5781:
5775:
5766:
5705:
5695:
5665:
5660:
5626:
5623:
5593:
5588:
5548:
5527:
5491:
5307:
5293:
5127:7β-Hydroxy-DHEA
5110:
4946:Levormeloxifene
4776:
4769:
4763:
4679:deoxymiroestrol
4547:-hinokiresinol)
4185:Methallenestril
4087:Doisynolic acid
3888:Methylestradiol
3403:7α-Hydroxy-DHEA
3294:
3284:
3276:
3246:
3241:
3180:
3040:
3021:
2974:
2955:Deoxymiroestrol
2943:
2925:
2902:
2879:
2846:
2832:
2809:
2778:
2710:
2672:
2644:
2602:
2597:
2567:
2558:
2556:
2552:
2551:
2547:
2510:
2506:
2500:
2496:
2491:
2487:
2442:
2435:
2398:
2394:
2389:
2385:
2344:
2340:
2301:
2297:
2291:
2287:
2280:
2264:
2260:
2215:
2211:
2174:
2170:
2133:
2129:
2092:
2088:
2043:
2039:
2002:
1998:
1961:
1957:
1920:
1916:
1879:
1875:
1835:
1831:
1794:
1790:
1751:
1747:
1716:(7): 1363S–8S.
1702:
1698:
1675:(11): 2037–43.
1661:
1657:
1610:
1606:
1553:
1549:
1510:
1506:
1469:
1465:
1426:
1417:
1394:(12): 3577–84.
1380:
1376:
1335:
1328:
1283:
1279:
1234:
1225:
1180:
1176:
1139:
1135:
1095:
1086:
1033:
1026:
1013:
1009:
1005:
958:
939:vaginal atrophy
931:
922:racemic mixture
887:
882:
868:equolifaciens,
769:Bifidobacterium
739:
695:
684:
672:
664:
655:bioavailability
643:
604:
593:. Relative to (
588:
567:
562:
518:
494:
445:
438:
433:
432:
431: ?)
422:
418:
414:
410:
396:
386:
380:
374:
366:
352:
349:
344:
339:
338:
327:
324:
323:
320:
314:
313:
310:
304:
303:
292:
274:
267:
258:
238:
225:
213:
174:
154:
134:
114:
103:
90:
76:
68:
67:
48:
17:
12:
11:
5:
6557:
6547:
6546:
6541:
6536:
6534:Phytoestrogens
6531:
6529:Isoflavandiols
6526:
6509:
6508:
6497:
6494:
6493:
6491:
6490:
6484:
6475:
6470:
6462:
6460:
6456:
6455:
6453:
6452:
6447:
6442:
6437:
6432:
6427:
6422:
6417:
6412:
6407:
6402:
6397:
6392:
6387:
6381:
6379:
6375:
6374:
6371:
6370:
6368:
6367:
6366:
6365:
6355:
6354:
6353:
6343:
6342:
6341:
6336:
6326:
6321:
6310:
6308:
6304:
6303:
6301:
6300:
6295:
6289:
6287:
6281:
6280:
6278:
6277:
6272:
6267:
6261:
6259:
6255:
6254:
6252:
6251:
6244:
6242:
6231:
6230:
6228:
6227:
6222:
6216:
6214:
6210:
6209:
6207:
6206:
6200:
6194:
6188:
6183:
6178:
6173:
6168:
6163:
6157:
6155:
6153:Phytoestrogens
6146:
6142:
6141:
6139:
6138:
6133:
6128:
6123:
6118:
6113:
6108:
6103:
6098:
6092:
6090:
6086:
6085:
6082:
6081:
6079:
6078:
6073:
6068:
6063:
6058:
6053:
6047:
6045:
6044:Fermented bean
6041:
6040:
6038:
6037:
6032:
6027:
6022:
6017:
6012:
6006:
6004:
6000:
5999:
5997:
5996:
5993:
5990:
5985:
5980:
5975:
5970:
5964:
5962:
5952:
5946:
5945:
5943:
5942:
5937:
5932:
5927:
5922:
5917:
5912:
5906:
5904:
5902:Meat analogues
5898:
5897:
5895:
5894:
5889:
5884:
5878:
5876:
5870:
5869:
5867:
5866:
5861:
5859:Tofu skin roll
5856:
5851:
5849:Sundubu jjigae
5846:
5841:
5836:
5831:
5826:
5821:
5816:
5811:
5806:
5801:
5796:
5791:
5785:
5783:
5777:
5776:
5769:
5767:
5765:
5764:
5759:
5754:
5749:
5744:
5739:
5734:
5729:
5724:
5719:
5713:
5711:
5707:
5706:
5694:
5693:
5686:
5679:
5671:
5662:
5661:
5659:
5658:
5653:
5648:
5643:
5637:
5635:
5628:
5627:
5622:
5621:
5614:
5607:
5599:
5590:
5589:
5587:
5586:
5581:
5576:
5571:
5566:
5561:
5557:
5554:
5553:
5550:
5549:
5547:
5546:
5541:
5535:
5533:
5529:
5528:
5526:
5525:
5520:
5515:
5510:
5505:
5499:
5497:
5493:
5492:
5490:
5489:
5484:
5479:
5474:
5469:
5464:
5459:
5454:
5444:
5439:
5434:
5429:
5424:
5419:
5417:Hydroxytyrosol
5414:
5409:
5404:
5399:
5394:
5389:
5384:
5379:
5374:
5369:
5355:
5350:
5345:
5340:
5335:
5330:
5325:
5319:
5317:
5310:
5299:
5298:
5295:
5294:
5292:
5291:
5282:
5281:
5272:
5271:
5266:
5261:
5256:
5251:
5246:
5241:
5236:
5231:
5226:
5221:
5216:
5211:
5206:
5201:
5196:
5191:
5186:
5164:
5159:
5154:
5149:
5144:
5139:
5134:
5132:Chloroindazole
5129:
5124:
5118:
5116:
5112:
5111:
5109:
5108:
5103:
5098:
5093:
5088:
5083:
5078:
5073:
5068:
5063:
5058:
5053:
5051:Spironolactone
5048:
5043:
5038:
5033:
5028:
5023:
5018:
5013:
5008:
5003:
4998:
4993:
4988:
4983:
4978:
4973:
4968:
4963:
4958:
4953:
4948:
4943:
4938:
4933:
4928:
4923:
4918:
4913:
4908:
4903:
4898:
4893:
4888:
4883:
4878:
4873:
4868:
4863:
4858:
4853:
4848:
4843:
4838:
4833:
4828:
4823:
4818:
4813:
4808:
4803:
4798:
4793:
4788:
4782:
4780:
4765:
4764:
4762:
4761:
4752:Others (e.g.,
4750:
4700:
4686:
4672:
4642:
4624:
4602:
4560:
4550:
4528:
4523:
4480:liquiritigenin
4389:
4375:
4353:
4327:Xenoestrogens:
4323:
4322:
4317:
4312:
4307:
4298:
4297:
4292:
4287:
4282:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4200:Paroxypropione
4197:
4192:
4187:
4182:
4177:
4169:
4161:
4156:
4151:
4150:
4149:
4139:
4134:
4129:
4124:
4119:
4114:
4112:Estrobin (DBE)
4109:
4104:
4099:
4094:
4089:
4084:
4079:
4074:
4069:
4068:
4067:
4057:
4056:
4055:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4003:Allenolic acid
4000:
3995:
3990:
3985:
3980:
3975:
3970:
3961:
3960:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3908:Norethisterone
3905:
3900:
3898:Mytatrienediol
3895:
3890:
3885:
3880:
3875:
3870:
3865:
3860:
3855:
3850:
3845:
3843:Ethylestradiol
3840:
3838:Ethinylestriol
3835:
3834:
3833:
3828:
3818:
3817:
3816:
3806:
3801:
3800:
3799:
3794:
3789:
3787:Estrone esters
3779:
3774:
3769:
3764:
3763:
3762:
3757:
3755:Estriol esters
3747:
3742:
3740:Estrapronicate
3737:
3732:
3727:
3726:
3725:
3720:
3715:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3662:
3657:
3652:
3647:
3642:
3637:
3632:
3631:
3630:
3620:
3615:
3610:
3605:
3600:
3595:
3565:
3560:
3558:Alestramustine
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3458:16-Ketoestrone
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3306:
3304:
3297:
3286:
3285:
3275:
3274:
3267:
3260:
3252:
3243:
3242:
3240:
3239:
3236:
3233:
3230:
3227:
3224:
3221:
3216:
3211:
3206:
3203:
3200:
3197:
3194:
3190:
3188:
3182:
3181:
3179:
3178:
3173:
3171:Propyl gallate
3168:
3163:
3158:
3153:
3148:
3143:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3088:
3083:
3078:
3073:
3068:
3063:
3058:
3052:
3050:
3046:
3045:
3042:
3041:
3039:
3038:
3036:-Penicillamine
3029:
3027:
3020:
3019:
3014:
3009:
3004:
2999:
2994:
2988:
2986:
2980:
2979:
2976:
2975:
2973:
2972:
2970:α-Isosparteine
2967:
2962:
2957:
2951:
2949:
2945:
2944:
2942:
2941:
2935:
2933:
2927:
2926:
2924:
2923:
2918:
2912:
2910:
2908:Flavonolignans
2904:
2903:
2901:
2900:
2895:
2889:
2887:
2881:
2880:
2878:
2877:
2872:
2867:
2862:
2856:
2854:
2848:
2847:
2842:
2840:
2834:
2833:
2831:
2830:
2825:
2819:
2817:
2811:
2810:
2808:
2807:
2802:
2788:
2786:
2780:
2779:
2777:
2776:
2771:
2766:
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2726:
2720:
2718:
2712:
2711:
2709:
2708:
2703:
2698:
2693:
2688:
2682:
2680:
2674:
2673:
2671:
2670:
2665:
2660:
2654:
2652:
2646:
2645:
2643:
2642:
2637:
2632:
2630:Liquiritigenin
2627:
2621:
2619:
2610:
2608:Phytoestrogens
2604:
2603:
2596:
2595:
2588:
2581:
2573:
2566:
2565:
2545:
2504:
2494:
2485:
2433:
2392:
2383:
2338:
2311:(5): 535–542.
2295:
2285:
2278:
2258:
2209:
2168:
2147:(8): 2188–93.
2127:
2086:
2057:(4): 400–419.
2037:
2016:(5): 1347–51.
1996:
1955:
1914:
1893:(10): 1710–5.
1873:
1829:
1808:(8): 2188–93.
1788:
1745:
1696:
1655:
1626:(4): 1029–37.
1604:
1567:(1–2): 71–83.
1547:
1504:
1463:
1415:
1374:
1326:
1277:
1223:
1194:(4): 1227–32.
1174:
1133:
1084:
1024:
1006:
1004:
1001:
1000:
999:
994:
989:
984:
979:
977:Liquiritigenin
974:
969:
964:
957:
954:
930:
927:
911:anti-oxidative
886:
883:
881:
880:Health effects
878:
842:
841:
839:Veillonella sp
836:
831:
826:
824:Slackia sp HE8
821:
816:
811:
806:
801:
796:
791:
786:
781:
776:
771:
766:
761:
756:
738:
735:
694:
691:
682:
670:
662:
642:
639:
602:
586:
566:
563:
561:
558:
517:
514:
493:
490:
443:
440:
439:
434:
412:
411:
407:standard state
404:
401:
400:
394:
388:
387:
384:
378:
372:
367:
362:
359:
358:
354:
353:
351:
350:
347:
345:
342:
334:
333:
332:
329:
328:
326:
325:
321:
318:
317:
315:
311:
308:
307:
299:
298:
297:
294:
293:
291:
290:
277:
275:
263:
260:
259:
257:
256:
248:
246:
240:
239:
237:
236:
228:
226:
218:
215:
214:
212:
211:
203:
201:
195:
194:
184:
176:
175:
173:
172:
164:
162:
156:
155:
153:
152:
144:
142:
136:
135:
133:
132:
125:
117:
115:
108:
105:
104:
102:
101:
93:
91:
86:
83:
82:
78:
77:
74:
70:
69:
57:
56:
50:
49:
42:
36:
35:
31:
30:
15:
9:
6:
4:
3:
2:
6556:
6545:
6542:
6540:
6537:
6535:
6532:
6530:
6527:
6525:
6524:GPER agonists
6522:
6521:
6519:
6506:
6495:
6488:
6485:
6483:
6479:
6476:
6474:
6471:
6469:
6468:
6464:
6463:
6461:
6457:
6451:
6450:Yeo Hiap Seng
6448:
6446:
6443:
6441:
6438:
6436:
6433:
6431:
6428:
6426:
6423:
6421:
6418:
6416:
6413:
6411:
6408:
6406:
6403:
6401:
6398:
6396:
6393:
6391:
6388:
6386:
6385:8th Continent
6383:
6382:
6380:
6376:
6364:
6361:
6360:
6359:
6356:
6352:
6349:
6348:
6347:
6346:Antinutrients
6344:
6340:
6337:
6335:
6332:
6331:
6330:
6327:
6325:
6322:
6319:
6318:Phospholipids
6315:
6312:
6311:
6309:
6305:
6299:
6296:
6294:
6291:
6290:
6288:
6286:
6282:
6276:
6273:
6271:
6268:
6266:
6263:
6262:
6260:
6256:
6249:
6246:
6245:
6243:
6240:
6236:
6232:
6226:
6223:
6221:
6218:
6217:
6215:
6211:
6204:
6201:
6198:
6195:
6192:
6189:
6187:
6184:
6182:
6179:
6177:
6174:
6172:
6169:
6167:
6164:
6162:
6159:
6158:
6156:
6154:
6150:
6147:
6143:
6137:
6134:
6132:
6129:
6127:
6124:
6122:
6119:
6117:
6114:
6112:
6109:
6107:
6104:
6102:
6099:
6097:
6094:
6093:
6091:
6087:
6077:
6074:
6072:
6069:
6067:
6064:
6062:
6059:
6057:
6054:
6052:
6049:
6048:
6046:
6042:
6036:
6033:
6031:
6028:
6026:
6023:
6021:
6018:
6016:
6013:
6011:
6008:
6007:
6005:
6001:
5994:
5991:
5989:
5986:
5984:
5981:
5979:
5976:
5974:
5971:
5969:
5966:
5965:
5963:
5960:
5956:
5953:
5947:
5941:
5940:Veggie burger
5938:
5936:
5933:
5931:
5928:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5907:
5905:
5903:
5899:
5893:
5890:
5888:
5885:
5883:
5880:
5879:
5877:
5875:
5871:
5865:
5862:
5860:
5857:
5855:
5852:
5850:
5847:
5845:
5842:
5840:
5837:
5835:
5832:
5830:
5827:
5825:
5822:
5820:
5817:
5815:
5812:
5810:
5807:
5805:
5802:
5800:
5799:Agedashi tofu
5797:
5795:
5792:
5790:
5787:
5786:
5784:
5778:
5773:
5763:
5760:
5758:
5755:
5753:
5750:
5748:
5745:
5743:
5740:
5738:
5735:
5733:
5730:
5728:
5725:
5723:
5720:
5718:
5715:
5714:
5712:
5708:
5703:
5699:
5692:
5687:
5685:
5680:
5678:
5673:
5672:
5669:
5657:
5656:Lonchocarpane
5654:
5652:
5649:
5647:
5644:
5642:
5639:
5638:
5636:
5633:
5629:
5620:
5615:
5613:
5608:
5606:
5601:
5600:
5597:
5585:
5582:
5580:
5577:
5575:
5572:
5570:
5567:
5565:
5562:
5559:
5558:
5555:
5545:
5542:
5540:
5537:
5536:
5534:
5530:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5506:
5504:
5501:
5500:
5498:
5494:
5488:
5485:
5483:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5463:
5460:
5458:
5455:
5452:
5448:
5445:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5395:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5373:
5370:
5367:
5363:
5359:
5356:
5354:
5351:
5349:
5346:
5344:
5341:
5339:
5336:
5334:
5331:
5329:
5326:
5324:
5321:
5320:
5318:
5314:
5311:
5306:
5300:
5290:
5287:
5284:
5283:
5280:
5277:
5274:
5273:
5270:
5267:
5265:
5262:
5260:
5257:
5255:
5252:
5250:
5247:
5245:
5242:
5240:
5237:
5235:
5232:
5230:
5227:
5225:
5222:
5220:
5217:
5215:
5212:
5210:
5207:
5205:
5202:
5200:
5197:
5195:
5192:
5190:
5187:
5184:
5180:
5176:
5172:
5168:
5165:
5163:
5160:
5158:
5155:
5153:
5150:
5148:
5145:
5143:
5140:
5138:
5135:
5133:
5130:
5128:
5125:
5123:
5120:
5119:
5117:
5113:
5107:
5104:
5102:
5099:
5097:
5094:
5092:
5089:
5087:
5084:
5082:
5079:
5077:
5074:
5072:
5069:
5067:
5064:
5062:
5059:
5057:
5054:
5052:
5049:
5047:
5044:
5042:
5039:
5037:
5034:
5032:
5031:Pipendoxifene
5029:
5027:
5024:
5022:
5019:
5017:
5014:
5012:
5009:
5007:
5004:
5002:
4999:
4997:
4994:
4992:
4989:
4987:
4984:
4982:
4979:
4977:
4974:
4972:
4969:
4967:
4964:
4962:
4959:
4957:
4954:
4952:
4949:
4947:
4944:
4942:
4939:
4937:
4934:
4932:
4929:
4927:
4924:
4922:
4919:
4917:
4914:
4912:
4909:
4907:
4904:
4902:
4899:
4897:
4894:
4892:
4889:
4887:
4884:
4882:
4879:
4877:
4874:
4872:
4869:
4867:
4866:Clomifenoxide
4864:
4862:
4859:
4857:
4854:
4852:
4849:
4847:
4844:
4842:
4841:Brilanestrant
4839:
4837:
4834:
4832:
4829:
4827:
4824:
4822:
4819:
4817:
4814:
4812:
4809:
4807:
4804:
4802:
4799:
4797:
4794:
4792:
4789:
4787:
4784:
4783:
4781:
4775:
4766:
4759:
4755:
4751:
4748:
4744:
4740:
4736:
4732:
4728:
4724:
4720:
4716:
4712:
4708:
4704:
4701:
4698:
4694:
4690:
4687:
4684:
4680:
4677:-like (e.g.,
4676:
4673:
4670:
4666:
4662:
4658:
4654:
4650:
4646:
4643:
4640:
4636:
4632:
4628:
4625:
4622:
4621:guggulsterone
4618:
4614:
4610:
4606:
4605:Phytosteroids
4603:
4600:
4596:
4592:
4588:
4584:
4580:
4576:
4572:
4568:
4564:
4561:
4558:
4554:
4551:
4548:
4546:
4540:
4539:enterolactone
4536:
4532:
4529:
4527:
4524:
4521:
4517:
4513:
4509:
4505:
4501:
4497:
4493:
4489:
4485:
4481:
4477:
4473:
4469:
4465:
4461:
4457:
4453:
4449:
4445:
4441:
4437:
4433:
4429:
4425:
4421:
4417:
4413:
4409:
4405:
4401:
4397:
4393:
4390:
4387:
4383:
4379:
4376:
4373:
4372:wedelolactone
4369:
4365:
4361:
4357:
4354:
4351:
4350:photoanethole
4347:
4343:
4339:
4335:
4331:
4328:
4325:
4324:
4321:
4318:
4316:
4313:
4311:
4308:
4306:
4303:
4300:
4299:
4296:
4293:
4291:
4288:
4286:
4283:
4281:
4278:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4236:
4233:
4231:
4228:
4226:
4223:
4221:
4218:
4216:
4213:
4211:
4208:
4206:
4205:Pentafluranol
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4174:
4170:
4168:
4166:
4162:
4160:
4157:
4155:
4152:
4148:
4145:
4144:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4108:
4105:
4103:
4100:
4098:
4095:
4093:
4090:
4088:
4085:
4083:
4080:
4078:
4075:
4073:
4070:
4066:
4063:
4062:
4061:
4058:
4054:
4051:
4050:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3965:Nonsteroidal:
3963:
3962:
3959:
3956:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3931:
3929:
3926:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3832:
3829:
3827:
3824:
3823:
3822:
3819:
3815:
3814:Ethandrostate
3812:
3811:
3810:
3807:
3805:
3802:
3798:
3795:
3793:
3790:
3788:
3785:
3784:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3761:
3758:
3756:
3753:
3752:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3724:
3721:
3719:
3716:
3714:
3711:
3710:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3667:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3629:
3626:
3625:
3624:
3623:Cloxestradiol
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3593:
3589:
3585:
3581:
3577:
3573:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3503:
3499:
3498:17α-Estradiol
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3308:
3307:
3305:
3301:
3298:
3293:
3287:
3283:
3280:
3273:
3268:
3266:
3261:
3259:
3254:
3253:
3250:
3237:
3234:
3231:
3228:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3207:
3204:
3201:
3198:
3195:
3192:
3191:
3189:
3187:
3183:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3087:
3084:
3082:
3079:
3077:
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3057:
3054:
3053:
3051:
3047:
3037:
3031:
3030:
3028:
3024:
3018:
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2989:
2987:
2985:
2984:Mycoestrogens
2981:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2952:
2950:
2946:
2940:
2937:
2936:
2934:
2932:
2928:
2922:
2921:Cinchonain-Ib
2919:
2917:
2914:
2913:
2911:
2909:
2905:
2899:
2898:Enterolactone
2896:
2894:
2891:
2890:
2888:
2886:
2882:
2876:
2875:Wedelolactone
2873:
2871:
2868:
2866:
2863:
2861:
2858:
2857:
2855:
2853:
2849:
2845:
2841:
2839:
2835:
2829:
2826:
2824:
2821:
2820:
2818:
2816:
2812:
2806:
2803:
2800:
2798:
2793:
2790:
2789:
2787:
2785:
2781:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2721:
2719:
2717:
2713:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2683:
2681:
2679:
2675:
2669:
2666:
2664:
2661:
2659:
2656:
2655:
2653:
2651:
2647:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2622:
2620:
2618:
2614:
2611:
2609:
2605:
2601:
2600:Xenoestrogens
2594:
2589:
2587:
2582:
2580:
2575:
2574:
2571:
2555:
2549:
2541:
2537:
2532:
2527:
2523:
2520:(in German).
2519:
2515:
2508:
2498:
2489:
2481:
2477:
2473:
2469:
2464:
2459:
2455:
2451:
2447:
2440:
2438:
2429:
2425:
2420:
2415:
2411:
2407:
2403:
2396:
2387:
2379:
2375:
2371:
2367:
2363:
2359:
2355:
2351:
2350:
2342:
2334:
2330:
2326:
2322:
2318:
2314:
2310:
2306:
2299:
2289:
2281:
2275:
2272:. CRC Press.
2271:
2270:
2262:
2254:
2250:
2245:
2240:
2236:
2232:
2228:
2224:
2220:
2213:
2205:
2201:
2196:
2191:
2188:(5): 1072–9.
2187:
2183:
2179:
2172:
2164:
2160:
2155:
2150:
2146:
2142:
2138:
2131:
2123:
2119:
2114:
2109:
2106:(9): 939–44.
2105:
2101:
2097:
2090:
2082:
2078:
2073:
2068:
2064:
2060:
2056:
2052:
2048:
2041:
2033:
2029:
2024:
2019:
2015:
2011:
2007:
2000:
1992:
1988:
1983:
1978:
1974:
1970:
1966:
1959:
1951:
1947:
1942:
1937:
1934:(2): 127–35.
1933:
1929:
1925:
1918:
1910:
1906:
1901:
1896:
1892:
1888:
1884:
1877:
1869:
1865:
1861:
1857:
1853:
1849:
1845:
1841:
1833:
1825:
1821:
1816:
1811:
1807:
1803:
1799:
1792:
1784:
1780:
1776:
1772:
1768:
1764:
1760:
1756:
1749:
1741:
1737:
1732:
1727:
1723:
1719:
1715:
1711:
1707:
1700:
1692:
1688:
1683:
1678:
1674:
1670:
1666:
1659:
1651:
1647:
1642:
1637:
1633:
1629:
1625:
1621:
1620:
1615:
1608:
1600:
1596:
1591:
1586:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1551:
1543:
1539:
1534:
1529:
1526:(5): 1072–9.
1525:
1521:
1520:
1515:
1508:
1500:
1496:
1491:
1486:
1482:
1478:
1474:
1467:
1459:
1455:
1451:
1447:
1443:
1439:
1436:(3): 155–70.
1435:
1431:
1424:
1422:
1420:
1411:
1407:
1402:
1397:
1393:
1389:
1385:
1378:
1370:
1366:
1362:
1358:
1354:
1350:
1347:(3): 569–78.
1346:
1342:
1341:
1333:
1331:
1322:
1318:
1313:
1308:
1304:
1300:
1296:
1292:
1288:
1281:
1273:
1269:
1264:
1259:
1255:
1251:
1247:
1243:
1239:
1232:
1230:
1228:
1219:
1215:
1210:
1205:
1201:
1197:
1193:
1189:
1185:
1178:
1170:
1166:
1161:
1156:
1152:
1148:
1144:
1137:
1129:
1125:
1121:
1117:
1113:
1109:
1105:
1101:
1093:
1091:
1089:
1080:
1076:
1071:
1066:
1062:
1058:
1054:
1050:
1046:
1042:
1038:
1031:
1029:
1021:
1017:
1011:
1007:
998:
995:
993:
990:
988:
985:
983:
980:
978:
975:
973:
970:
968:
965:
963:
960:
959:
953:
951:
947:
942:
940:
936:
926:
923:
918:
916:
912:
908:
904:
900:
896:
892:
877:
875:
871:
867:
866:Adlercreutzia
863:
859:
855:
851:
850:Lactobacillus
847:
840:
837:
835:
832:
830:
827:
825:
822:
820:
817:
815:
812:
810:
807:
805:
802:
800:
797:
795:
792:
790:
787:
785:
782:
780:
777:
775:
772:
770:
767:
765:
762:
760:
757:
755:
752:
751:
750:
748:
744:
734:
732:
728:
724:
720:
716:
712:
708:
704:
700:
697:To produce (
690:
688:
680:
676:
668:
660:
656:
652:
648:
638:
636:
632:
628:
624:
620:
616:
612:
608:
600:
596:
592:
584:
580:
576:
573:)-equol is a
572:
557:
555:
551:
547:
543:
539:
535:
531:
528:)-equol and (
527:
523:
513:
511:
507:
503:
499:
489:
487:
484:
481:, equol is a
480:
476:
472:
468:
464:
460:
456:
453:
452:isoflavandiol
449:
437:
430:
425:
408:
402:
395:
393:
390:
389:
368:
365:
361:
360:
355:
346:
341:
340:
337:
330:
316:
306:
305:
302:
295:
287:
283:
282:DTXSID0022309
279:
278:
276:
266:
262:
261:
254:
250:
249:
247:
245:
242:
241:
234:
230:
229:
227:
221:
217:
216:
209:
205:
204:
202:
200:
197:
196:
192:
188:
185:
183:
181:ECHA InfoCard
178:
177:
170:
166:
165:
163:
161:
158:
157:
150:
146:
145:
143:
141:
138:
137:
130:
126:
123:
119:
118:
116:
112:
107:
106:
99:
95:
94:
92:
89:
85:
84:
79:
71:
65:
61:
55:
51:
46:
41:
37:
32:
28:
23:
6482:Akiko Aoyagi
6465:
6420:Plamil Foods
6400:Gardenburger
6314:Soy lecithin
6270:Lipoxygenase
6265:Beta-amylase
6199:(metabolite)
6193:(metabolite)
6190:
6145:Biochemicals
5892:Vegan cheese
5864:Yong tau foo
5757:Soybean meal
5732:Soy molasses
5701:
5640:
5376:
5285:
5275:
5199:Mepitiostane
5147:Epitiostanol
5016:Ormeloxifene
4941:Lasofoxifene
4851:Camizestrant
4846:Broparestrol
4836:Bazedoxifene
4758:rotundifuran
4707:alkylphenols
4657:β-zearalenol
4653:α-zearalenol
4639:stigmasterol
4631:β-sitosterol
4627:Phytosterols
4595:triclocarban
4591:methoxychlor
4544:
4526:Lavender oil
4520:tectorigenin
4452:formononetin
4447:
4326:
4301:
4172:
4164:
3964:
3948:Quinestradol
3938:Promestriene
3913:Noretynodrel
3777:Estromustine
3730:Estramustine
3665:
3572:testosterone
3309:
3131:Methoxychlor
3056:Alkylphenols
3017:β-Zearalenol
3012:β-Zearalanol
3007:α-Zearalenol
2796:
2791:
2774:Tectorigenin
2739:Formononetin
2557:. Retrieved
2548:
2524:(1): 13–22.
2521:
2517:
2507:
2497:
2488:
2453:
2449:
2409:
2405:
2395:
2386:
2353:
2347:
2341:
2308:
2304:
2298:
2288:
2268:
2261:
2226:
2222:
2212:
2185:
2181:
2171:
2144:
2140:
2130:
2103:
2099:
2089:
2054:
2050:
2040:
2013:
2009:
1999:
1972:
1968:
1958:
1931:
1927:
1917:
1890:
1886:
1876:
1846:(1): 27–32.
1843:
1839:
1832:
1805:
1801:
1791:
1761:(3): 335–9.
1758:
1754:
1748:
1713:
1709:
1699:
1672:
1668:
1658:
1623:
1617:
1607:
1564:
1560:
1550:
1523:
1517:
1507:
1483:(1): 14–25.
1480:
1477:Toxicol. Sci
1476:
1466:
1433:
1429:
1391:
1387:
1377:
1344:
1338:
1297:(2): 353–7.
1294:
1290:
1280:
1245:
1241:
1191:
1187:
1177:
1153:(6): 873–6.
1150:
1146:
1136:
1103:
1099:
1047:(1): 214–9.
1044:
1040:
1019:
1010:
943:
932:
919:
917:properties.
903:peroxidation
888:
857:
843:
746:
740:
730:
722:
710:
706:
698:
696:
686:
658:
646:
644:
622:
606:
598:
594:
577:, selective
575:nonsteroidal
570:
568:
560:Pharmacology
549:
541:
537:
533:
529:
525:
519:
501:
497:
495:
483:nonsteroidal
461:, a type of
447:
446:
149:ChEMBL198877
81:Identifiers
73:Other names
63:
59:
44:
6395:Boca Burger
6334:Tocopherols
6126:Stinky tofu
6089:Other foods
6015:Doubanjiang
5854:Tahu goreng
5814:Dubu kimchi
5762:Soybean oil
5742:Soy protein
5717:Soy allergy
5702:Glycine max
5651:Laxiflorane
5632:Isoflavanes
5625:Isoflavanes
5544:Zearalenone
5496:Antagonists
5472:Resveratrol
5437:Nonylphenol
5432:Niacinamide
5348:Bisphenol A
5338:Aldosterone
5167:Glyceollins
5115:Antagonists
5106:Zuclomifene
5101:Zindoxifene
5011:NNC 45-1506
5006:NNC 45-0781
5001:NNC 45-0320
4996:NNC 45-0095
4991:Nitromifene
4971:Miproxifene
4921:Fispemifene
4896:Enclomifene
4891:Droloxifene
4871:CN-55945-27
4816:Afimoxifene
4806:Acefluranol
4697:rhaponticin
4693:resveratrol
4689:Stilbenoids
4661:zearalenone
4649:zearalanone
4635:campesterol
4567:alternariol
4500:pinocembrin
4444:epicatechin
4416:biochanin A
4356:Chalconoids
4250:Terfluranol
4225:Quadrosilan
4097:Elacestrant
3998:Allenestrol
3873:Lynestrenol
3797:Estropipate
3767:Estrofurate
3618:Clomestrone
3598:Atrimustine
3548:Abiraterone
3502:alfatradiol
3136:Nonylphenol
3116:Erythrosine
3081:Bisphenol S
3076:Bisphenol F
3071:Bisphenol A
3026:Derivatives
2997:Zearalenone
2992:Zearalanone
2965:Resveratrol
2838:Isoflavenes
2784:Isoflavanes
2724:Biochanin A
2716:Isoflavones
2640:Pinocembrin
1975:(2): 86–9.
1147:Br. J. Nutr
885:Skin health
854:Eggerthella
727:antibiotics
532:)-equol. (
522:enantiomers
357:Properties
187:100.007.749
6518:Categories
5951:condiments
5949:Sauces and
5887:Soy yogurt
5874:Plant milk
5839:Mapo doufu
5722:Soy candle
5487:Tectoridin
5467:Raloxifene
5442:Oleuropein
5289:Trilostane
5234:Prochloraz
5194:MDL-101906
5189:ICI-164384
5076:Trioxifene
5071:Toremifene
5041:Raloxifene
5026:Panomifene
5021:Ospemifene
4986:Nafoxidine
4876:Cyclofenil
4831:Arzoxifene
4811:Acolbifene
4743:phthalates
4711:bisphenols
4683:miroestrol
4587:methiocarb
4575:endosulfan
4563:Pesticides
4535:enterodiol
4516:tectoridin
4496:penduletin
4492:naringenin
4476:kaempferol
4392:Flavonoids
4386:psoralidin
4382:coumestrol
4378:Coumestans
4342:dianethole
4295:WAY-214156
4285:WAY-200070
4280:WAY-169916
4275:WAY-166818
4245:SKF-82,958
4210:Phenestrol
4190:Methestrol
4175:-Hexestrol
4167:-Butestrol
4048:Dienestrol
4028:Carbestrol
4013:Bifluranol
4008:Benzestrol
3953:Quinestrol
3903:Nilestriol
3745:Estrazinol
3678:Epimestrol
3668:-Estradiol
3650:Cyclotriol
3588:nandrolone
3563:Almestrone
3398:7-Oxo-DHEA
3310:Steroidal:
3282:modulators
3166:Phthalates
3121:Heptachlor
3111:Enzacamene
3106:Endosulfan
2960:Miroestrol
2893:Enterodiol
2865:Coumestrol
2852:Coumestans
2635:Naringenin
2625:Hesperetin
2617:Flavanones
2559:2023-11-17
1003:References
992:WAY-200070
987:Prinaberel
935:menopausal
891:anti-aging
651:absorption
597:)-equol, (
471:intestines
463:isoflavone
392:Molar mass
253:2T6D2HPX7Q
160:ChemSpider
109:3D model (
88:CAS Number
40:IUPAC name
6378:Companies
6363:Cystatins
6171:Glycitein
6161:Genistein
6131:Tofu skin
6106:Soy flour
5959:Soy sauce
5910:Beanfeast
5844:Miso soup
5834:Kongnamul
5829:Kongguksu
5824:Hiyayakko
5780:Soy-based
5737:Soy paint
5646:Glabridin
5482:Tamoxifen
5462:Quercetin
5402:Genistein
5382:Estradiol
5366:o',p'-DDE
5269:ZK-191703
5264:ZK-164015
5224:Phenytoin
5122:(R,R)-THC
5061:Tamoxifen
5036:Promensil
4961:LY-117018
4936:Idoxifene
4931:ICI-55548
4916:Femarelle
4901:Endoxifen
4861:Clomifene
4617:diosgenin
4613:digitalis
4609:digitoxin
4599:triclosan
4579:fenarimol
4512:quercetin
4488:myricetin
4484:mirificin
4472:glycitein
4464:genistein
4460:glabridin
4420:calycosin
4408:baicalein
4364:phloretin
4320:ZK-283197
4180:Mestilbol
4142:Hexestrol
4117:Fenestrel
4092:Efavirenz
4023:Butestrol
3978:2,8-DHHHC
3973:(S,S)-THC
3968:(R,R)-THC
3923:Pentolame
3918:Orestrate
3893:Moxestrol
3883:Mestranol
3848:Etynodiol
3708:Estradiol
3683:Equilenin
3645:Cyclodiol
3603:Bolandiol
3193:Aluminium
3049:Synthetic
2939:Quercetin
2931:Flavonols
2860:Coumestan
2828:Phlorizin
2823:Phloretin
2805:Glabridin
2754:Glycitein
2744:Genistein
2668:Mirificin
2540:1996-1553
2472:1388-0209
2428:2079-9284
2412:(1): 16.
2406:Cosmetics
2378:205668316
2356:: 36–54.
2293:1548-1553
1581:0303-7207
1120:0968-0896
972:Genistein
743:genistein
675:glycoside
665:(rate of
653:and high
637:(GPR30).
611:estradiol
546:estradiol
475:estradiol
465:found in
6405:Kikkoman
6351:Phytates
6316:(mix of
6250:(lectin)
6225:Glycinin
6205:(leaves)
6186:Daidzein
6176:Glycitin
6166:Genistin
6121:Soy pulp
6096:Mamenori
6010:Doenjang
5988:Teriyaki
5930:Tofurkey
5882:Soy milk
5794:Aburaage
5752:Diseases
5560:See also
5362:p,p'-DDT
5353:Daidzein
5343:Atrazine
5316:Agonists
5244:RU-58668
5239:RU-39411
5086:U-11555A
5081:TZE-5323
4826:Anordrin
4821:Anordiol
4754:agnuside
4731:parabens
4571:dieldrin
4543:nyasol (
4508:puerarin
4504:prunetin
4468:genistin
4456:glabrene
4428:daidzein
4424:catechin
4412:baicalin
4404:apigenin
4334:anethole
4122:FERb 033
3958:Tibolone
3943:RU-16117
3928:Prodiame
3863:Hippulin
3858:Hexolame
3703:Estetrol
3613:Butolame
3303:Agonists
3238:Vanadate
3232:Selenite
3209:Chromium
3199:Arsenite
3196:Antimony
3141:Parabens
3096:Dieldrin
3061:Atrazine
2844:Glabrene
2769:Puerarin
2764:Prunetin
2749:Genistin
2729:Daidzein
2706:Icaritin
2658:Acacetin
2650:Flavones
2480:23862588
2370:27521253
2333:44910993
2325:28574180
2253:20519412
2204:15883431
2163:16857839
2122:19321575
2081:20347861
2032:16614428
1991:15067102
1950:10778038
1868:10603402
1860:10798213
1824:16857839
1783:23496918
1740:20519411
1691:19776178
1650:19710188
1599:24530924
1542:15883431
1499:15084758
1458:14112442
1450:15734719
1410:12468591
1272:20519412
1218:16744928
1169:16351761
1128:15018930
1079:15640190
962:Daidzein
956:See also
952:levels.
895:telomere
860:)-equol.
715:daidzein
679:aglycone
657:. When (
506:estrogen
486:estrogen
479:steroids
467:soybeans
459:daidzein
455:estrogen
98:531-95-3
6440:Vitasoy
6435:Tofutti
6430:So Good
6415:Mr Bean
6339:Sterols
6324:Lunasin
6258:Enzymes
6239:lectins
6203:Daidzin
6116:Soy nut
5995:Yìn yóu
5968:Ganjang
5819:Edamame
5747:Soybean
5727:Soy ink
5710:General
5532:Unknown
5508:Estriol
5412:GPER-L2
5407:GPER-L1
5091:U-11634
4966:Menerba
4956:LN-2299
4951:LN-1643
4926:GW-7604
4881:D-15413
4713:(e.g.,
4705:(e.g.,
4691:(e.g.,
4675:Steroid
4647:(e.g.,
4629:(e.g.,
4607:(e.g.,
4565:(e.g.,
4557:cadmium
4555:(e.g.,
4533:(e.g.,
4531:Lignans
4432:daidzin
4396:7,8-DHF
4394:(incl.
4380:(e.g.,
4358:(e.g.,
4240:SERBA-2
4235:SC-4289
4230:SC-3296
4137:GTx-758
4033:D-15414
3983:β-LGND1
3933:Prolame
3782:Estrone
3750:Estriol
3688:Equilin
3570:(e.g.,
3483:16α-LE2
3226:Mercury
3205:Cadmium
3126:Lindane
3101:Dioxins
2916:Silybin
2885:Lignans
2734:Daidzin
2244:2884333
2072:3074428
1909:9772140
1775:9492344
1731:2884334
1641:2744624
1590:4040308
1369:4467689
1361:6383008
1321:7082293
1312:1163650
1263:2884333
1209:1261026
1049:Bibcode
982:Menerba
719:Seaweed
633:of the
631:agonist
579:agonist
492:History
429:what is
427: (
397:242.274
220:PubChem
6503:
6445:Yamasa
6181:Ononin
6066:Kinema
6061:Douchi
6051:Akhuni
6003:Pastes
5983:Tamari
5915:Tempeh
5809:Douhua
5804:Bai ye
5782:dishes
5427:Niacin
5422:Kepone
5279:ERX-11
5249:SS1020
5157:ERB-88
5152:ERA-90
5056:SS1010
4981:MRL-37
4346:dianol
4315:ERB-79
4310:ERA-45
4305:ERB-26
4038:DCW234
3993:AC-186
3660:DHEA-S
3592:esters
3576:esters
3428:8β-VE2
3229:Nickel
3219:Copper
3214:Cobalt
3202:Barium
2948:Others
2799:-Equol
2759:Ononin
2538:
2478:
2470:
2426:
2376:
2368:
2331:
2323:
2276:
2251:
2241:
2202:
2161:
2120:
2079:
2069:
2030:
1989:
1948:
1907:
1866:
1858:
1822:
1781:
1773:
1738:
1728:
1689:
1648:
1638:
1597:
1587:
1579:
1540:
1497:
1456:
1448:
1408:
1367:
1359:
1319:
1309:
1270:
1260:
1216:
1206:
1167:
1126:
1118:
1077:
1070:544246
1067:
424:verify
421:
336:SMILES
208:C14131
140:ChEMBL
34:Names
20:Equol
6487:Yuasa
6459:Other
6390:Alpro
6307:Other
6197:O-DMA
6191:Equol
6101:Oncom
6076:Nattō
6071:Tauco
6035:Tương
5992:Tsuyu
5973:Ponzu
5961:based
5641:Equol
5503:CCL18
5377:Equol
5259:ZB716
5229:PHTPP
5096:Y-134
4773:SERMs
4768:Mixed
4448:equol
4330:Anise
4159:M2613
2792:Equol
2502:et.al
2374:S2CID
2329:S2CID
1864:S2CID
1779:S2CID
1454:S2CID
1365:S2CID
508:- or
448:Equol
301:InChI
233:91469
169:82594
111:JSmol
6480:and
6425:Silk
6235:PHAs
6020:Miso
5925:Tofu
5523:MIBE
5518:G-36
5513:G-15
5447:PCBs
5304:GPER
5214:MIBE
4747:PCBs
4739:PHBA
4735:PBBs
4583:HPTE
4440:EGCG
4338:anol
4173:meso
4165:meso
3655:DHEA
3590:and
3574:and
3223:Lead
3161:PHBA
3151:PCBs
3146:PBBs
2536:ISSN
2476:PMID
2468:ISSN
2424:ISSN
2366:PMID
2321:PMID
2274:ISBN
2249:PMID
2200:PMID
2159:PMID
2118:PMID
2077:PMID
2028:PMID
1987:PMID
1946:PMID
1905:PMID
1856:PMID
1820:PMID
1771:PMID
1736:PMID
1687:PMID
1646:PMID
1595:PMID
1577:ISSN
1538:PMID
1495:PMID
1446:PMID
1406:PMID
1357:PMID
1317:PMID
1268:PMID
1214:PMID
1165:PMID
1124:PMID
1116:ISSN
1075:PMID
913:and
872:and
635:GPER
477:are
244:UNII
199:KEGG
5698:Soy
5477:STX
5397:G-1
5358:DDT
5179:III
4727:DDT
4725:),
4723:BPS
4719:BPF
4715:BPA
4615:),
4545:cis
4436:ECG
3666:ent
3235:Tin
3091:DDT
3086:DDE
3066:BHA
2526:doi
2458:doi
2414:doi
2358:doi
2313:doi
2239:PMC
2231:doi
2227:140
2190:doi
2149:doi
2145:136
2108:doi
2104:139
2067:PMC
2059:doi
2018:doi
2014:136
1977:doi
1936:doi
1895:doi
1891:128
1848:doi
1810:doi
1806:136
1763:doi
1759:217
1726:PMC
1718:doi
1714:140
1677:doi
1673:139
1636:PMC
1628:doi
1585:PMC
1569:doi
1565:389
1528:doi
1485:doi
1438:doi
1434:230
1396:doi
1392:132
1349:doi
1307:PMC
1299:doi
1295:201
1258:PMC
1250:doi
1246:140
1204:PMC
1196:doi
1155:doi
1108:doi
1065:PMC
1057:doi
683:max
671:max
663:max
591:ERα
583:ERβ
581:of
548:. (
524:: (
270:EPA
223:CID
6520::
5364:,
5183:IV
5181:,
5177:,
5175:II
5173:,
4756:,
4745:,
4741:,
4737:,
4733:,
4729:,
4721:,
4717:,
4709:,
4695:,
4681:,
4667:,
4663:,
4659:,
4655:,
4651:,
4637:,
4633:,
4619:,
4597:,
4593:,
4589:,
4585:,
4581:,
4577:,
4573:,
4569:,
4541:,
4537:,
4518:,
4514:,
4510:,
4506:,
4502:,
4498:,
4494:,
4490:,
4486:,
4482:,
4478:,
4474:,
4470:,
4466:,
4462:,
4458:,
4454:,
4450:,
4446:,
4442:,
4438:,
4434:,
4430:,
4426:,
4422:,
4418:,
4414:,
4410:,
4406:,
4402:,
4398:,
4384:,
4370:,
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4362:,
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4340:,
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3586:,
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3291:ER
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