2768:
2730:
2656:
2958:
2691:
2919:
2996:
2877:
1113:
2816:
2809:
314:
179:
38:
744:
3006:
29:
2619:
2929:
1023:
2681:
499:
1109:. Asparagine is synthesized by amidation of aspartate, with glutamine donating the NH4. These are nonessential amino acids, and their simple biosynthetic pathways occur in all organisms. Methionine, threonine, lysine, isoleucine, valine, and leucine are essential amino acids in humans and most vertebrates. Their biosynthetic pathways in bacteria are complex and interconnected.
1080:
malate using NADH. Then the malate is decarboxylated to pyruvate. Now this pyruvate can easily enter the mitochondria, where it is carboxylated again to oxaloacetate by pyruvate carboxylase. In this way, the transfer of acetyl-CoA that is from the mitochondria into the cytoplasm produces a molecule of NADH. The overall reaction, which is spontaneous, may be summarized as:
2968:
1059:. Some intermediate steps of the cycle are slightly different from the citric acid cycle; nevertheless oxaloacetate has the same function in both processes. This means that oxaloacetate in this cycle also acts as the primary reactant and final product. In fact the oxaloacetate is a net product of the
1075:
resides. The acetyl-CoA is transported as a citrate, which has been previously formed in the mitochondrial matrix from acetyl-CoA and oxaloacetate. This reaction usually initiates the citric acid cycle, but when there is no need of energy it is transported to the cytoplasm where it is broken down to
2887:
1079:
Another part of the cycle requires NADPH for the synthesis of fatty acids. Part of this reducing power is generated when the cytosolic oxaloacetate is returned to the mitochondria as long as the internal mitochondrial layer is non-permeable for oxaloacetate. Firstly the oxaloacetate is reduced to
2797:
2720:
2646:
2758:
2846:
1633:
1171:
2174:
1778:
2767:
2729:
2655:
2368:
van Vugt-Lussenburg, BMA; van der Weel, L; Hagen, WR; Hagedoorn, P-L (26 February 2021), "Biochemical
Similarities and Differences between the Catalytic Cluster Containing Fumarases FumA and FumB from
2957:
2227:
2224:
2212:
2192:
2188:
1831:
1828:
1816:
1796:
1792:
1706:
1244:
2222:
1826:
3051:
2690:
2546:"Fungal production of citric and oxalic acid: importance in metal speciation, physiology and biogeochemical processes" Advances in Microbial Physiology (1999), 41, 47-92.
2511:
2555:
Xu, Hua-Wei. "Oxalate accumulation and regulations is independent of glycolate oxidase in rice leaves" Journal of
Experimental Botany, Vol 57, No. 9 pp. 1899-1908, 2006
2918:
3175:
2995:
2876:
943:, malate is oxidized to oxaloacetate again using NAD+. Then oxaloacetate remains in the cytosol, where the rest of reactions will take place. Oxaloacetate is later
1708:
1246:
2225:
2216:
2186:
2185:
2181:
1829:
1820:
1790:
1789:
1785:
979:
using one ammonium molecule from degraded amino acids, another ammonium group from aspartate and one bicarbonate molecule. This route commonly occurs in
512:
1656:
1653:
1194:
1191:
1112:
3044:
2189:
1793:
1665:
1203:
2204:
1808:
1694:
1232:
1003:. Malate is acted on by malate dehydrogenase to become oxaloacetate, producing a molecule of NADH. After that, oxaloacetate will be recycled to
3037:
2220:
2207:
2193:
1824:
1811:
1797:
353:
1673:
1211:
2583:
2223:
1827:
1637:
1175:
1684:
1222:
1675:
1661:
1645:
1213:
1199:
1183:
1681:
1640:
1219:
1178:
1705:
1668:
1243:
1206:
2209:
1813:
1696:
1695:
1679:
1672:
1669:
1234:
1233:
1217:
1210:
1207:
2421:"Direct demonstration of enol-oxaloacetate as an immediate product of malate oxidation by the mammalian succinate dehydrogenase"
2230:
2202:
2177:
1834:
1806:
1781:
1703:
1702:
1700:
1658:
1636:
1241:
1240:
1238:
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1174:
2215:
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1819:
1782:
1657:
1639:
1195:
1177:
462:
2519:
1649:
1648:
1187:
1186:
3246:
1707:
1655:
1245:
1193:
435:
215:
507:
3808:
3559:
3150:
2217:
2182:
1821:
1786:
1662:
1644:
1200:
1182:
3155:
2233:
2232:
2191:
2179:
1837:
1836:
1795:
1783:
1676:
1641:
1214:
1179:
2201:
1805:
1704:
1671:
1667:
1660:
1242:
1209:
1205:
1198:
116:
2231:
2184:
1835:
1788:
1682:
1674:
1638:
1220:
1212:
1176:
2352:
2218:
1822:
1687:
1225:
952:
328:
2236:
2219:
2213:
2208:
2206:
2198:
1840:
1823:
1817:
1812:
1810:
1802:
1677:
1666:
1650:
1215:
1204:
1188:
3828:
2237:
2234:
2197:
1841:
1838:
1801:
1643:
1181:
907:
is a metabolic pathway consisting of a series of eleven enzyme-catalyzed reactions, resulting in the generation of
2228:
1832:
519:
3381:
2576:
1709:
1664:
1247:
1202:
835:
2239:
2238:
2229:
2199:
2194:
1843:
1842:
1833:
1803:
1798:
1693:
1654:
1231:
1192:
2235:
2221:
2203:
2196:
2187:
2183:
2180:
1839:
1825:
1807:
1800:
1791:
1787:
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1701:
1685:
1683:
1678:
1647:
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1239:
1223:
1221:
1216:
1185:
1180:
2226:
2210:
2205:
2200:
2195:
1830:
1814:
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1663:
1659:
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1237:
1236:
1235:
1230:
1229:
1228:
1218:
1208:
1201:
1197:
1190:
1189:
1184:
3410:
2214:
2211:
2190:
1818:
1815:
1794:
1689:
1688:
1686:
1227:
1226:
1224:
3540:
271:
174:
2493:
1632:
1170:
3813:
3718:
3251:
1105:. Aspartate and alanine are formed from oxaloacetate and pyruvate, respectively, by transamination from
292:
37:
2569:
3818:
3607:
3515:
3241:
3165:
2311:
1102:
721:
186:
3190:
3823:
3728:
3535:
3391:
3170:
747:
725:
309:
3594:
3574:
3530:
3358:
3131:
3012:
781:
3029:
3783:
3662:
3639:
3477:
3386:
3313:
3218:
3106:
3066:
2815:
2808:
2258:
960:
924:
791:
570:
3629:
28:
3833:
3599:
3275:
2543:
956:
3074:
3063:
2432:
920:
912:
889:
885:
777:
590:
586:
280:
50:
1071:
In previous stages acetyl-CoA is transferred from the mitochondria to the cytoplasm where
8:
3775:
3564:
3256:
3236:
1072:
831:
156:
92:
82:
2468:
2436:
313:
178:
136:
3185:
2397:
2301:
2561:
1749:
1732:
1719:
3723:
3681:
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2592:
2450:
2445:
2420:
2402:
2348:
2316:
2279:
2262:
2249:
857:
594:
963:(GTP) as phosphate source. Glucose is obtained after further downstream processing.
911:
from non-carbohydrates substrates. The beginning of this process takes place in the
3231:
3111:
2440:
2392:
2382:
1060:
1052:
1036:
881:
869:
752:
582:
547:
543:
376:
3525:
3333:
2387:
1056:
904:
873:
574:
260:
3520:
3160:
3121:
2974:
1728:
948:
944:
841:
563:
490:
1763:
Click on genes, proteins and metabolites below to link to respective articles.
1156:
Click on genes, proteins and metabolites below to link to respective articles.
3802:
3705:
3672:
3634:
3492:
3376:
2894:
2367:
845:
606:
419:
167:
3743:
3621:
3497:
3328:
3261:
3126:
3116:
3096:
2789:
2638:
2406:
1141:
1008:
936:
743:
3180:
2454:
2173:
1777:
1144:. This enzyme is seen in plants, but is not known in the animal kingdom.
3473:
980:
1063:
because its loop of the cycle incorporates two molecules of acetyl-CoA.
765:
Oxaloacetate forms in several ways in nature. A principal route is upon
3753:
3584:
3569:
3550:
3449:
3444:
3439:
3338:
3226:
3205:
3078:
3060:
2935:
2829:
2611:
2306:
972:
893:
877:
861:
770:
578:
399:
205:
187:
147:
3005:
2967:
1101:
Six essential amino acids and three nonessential are synthesized from
3653:
3469:
3434:
3367:
3353:
2886:
2750:
1106:
1012:
1004:
935:. This transformation is needed to transport the molecule out of the
827:
784:
in a slow reaction with the initial product being enol-oxaloacetate.
766:
2796:
2719:
2645:
987:, and NADH can be produced in two different ways. One of these uses
489:
Except where otherwise noted, data are given for materials in their
3709:
3696:
3643:
3465:
3429:
3420:
3324:
3285:
3101:
2712:
2618:
1048:
1040:
1016:
1000:
992:
927:
and water. This reaction results in the formation of oxaloacetate.
916:
787:
737:
733:
235:
115:
3401:
3320:
3299:
3290:
3209:
3195:
3141:
3059:
2928:
2852:
2757:
940:
908:
865:
610:
409:
247:
2680:
1022:
3506:
3304:
3087:
2845:
2673:
1138:
1044:
1026:
Relationship of oxaloacetic acid, malic acid, and aspartic acid
996:
932:
919:
molecules are found. A pyruvate molecule is carboxylated by a
2418:
127:
105:
297:
2277:
The interactive pathway map can be edited at WikiPathways:
1747:
The interactive pathway map can be edited at WikiPathways:
984:
976:
928:
717:
226:
573:
in many processes that occur in animals. It takes part in
2512:"Animo acids synthesized from oxaloacetate and pyruvate"
975:
is a metabolic pathway that results in the formation of
2591:
780:, in the citric acid cycle. Malate is also oxidized by
681:
1015:
over the others. This recycling maintains the flow of
337:
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
720:forms of oxaloacetic acid are particularly stable.
214:
983:. The reactions related to the urea cycle produce
3800:
1039:is a variant of the citric acid cycle. It is an
790:with carbonic acid, driven by the hydrolysis of
259:
2176:
1780:
1635:
1173:
91:
3298:
2347:(4th ed.). New York: W. H. Freeman.
3045:
2577:
1125:Oxaloacetate produces oxalate by hydrolysis.
1116:Oxaloacetate and pyruvate aminoacid synthesis
892:. Oxaloacetate is also a potent inhibitor of
2271:
995:molecules. Fumarate can be transformed into
1741:
3052:
3038:
2584:
2570:
2343:Nelson, David L.; Cox, Michael M. (2005).
1147:
312:
177:
155:
2444:
2396:
2386:
2381:(2) (published 6 February 2013): e55549,
2342:
1076:cytoplasmic acetyl-CoA and oxaloacetate.
750:catalyzed creation of enol-oxaloacetate.
562:H. Oxaloacetic acid, in the form of its
279:
2419:M.V. Panchenko; A.D. Vinogradov (1991).
1021:
923:enzyme, activated by a molecule each of
851:
786:It also arises from the condensation of
742:
1120:
1096:
1066:
856:Oxaloacetate is an intermediate of the
308:
3801:
2338:
2336:
2334:
2332:
605:Oxaloacetic acid undergoes successive
424:161 Ā°C (322 Ā°F; 434 K)
168:
3247:2-Amino-3-carboxymuconic semialdehyde
3033:
2565:
1718:|alt=Glycolysis and Gluconeogenesis
1088:+ ATP + acetyl-CoA ā ADP + P
830:of plants, this process proceeds via
732:-Enol-oxaloacetate also appears when
340:Key: KHPXUQMNIQBQEV-UHFFFAOYSA-N
135:
3560:2,3-Dihydroxy-3-methylpentanoic acid
684:, the enolizable proton is ionized:
2329:
1030:
250:
234:
13:
2172:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2125:
2120:
2115:
2110:
2105:
2100:
2095:
2090:
2085:
2080:
2075:
2070:
2065:
2060:
2055:
2050:
2045:
2040:
2035:
2030:
2025:
2020:
2015:
2010:
2005:
2000:
1995:
1990:
1985:
1980:
1975:
1970:
1965:
1960:
1955:
1950:
1945:
1940:
1935:
1930:
1925:
1920:
1915:
1910:
1905:
1900:
1895:
1890:
1885:
1880:
1875:
1870:
1865:
1860:
1855:
1850:
1776:
1631:
1624:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1569:
1564:
1559:
1554:
1549:
1544:
1539:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1499:
1494:
1489:
1484:
1479:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1439:
1434:
1429:
1424:
1419:
1414:
1409:
1404:
1399:
1394:
1389:
1384:
1379:
1374:
1369:
1364:
1359:
1354:
1349:
1344:
1339:
1334:
1329:
1324:
1319:
1314:
1309:
1304:
1299:
1294:
1289:
1284:
1279:
1274:
1269:
1264:
1259:
1254:
1169:
1111:
899:
14:
3845:
1750:"GlycolysisGluconeogenesis_WP534"
1137:This process is catalyzed by the
953:phosphoenolpyruvate carboxykinase
840:Oxaloacetate can also arise from
3004:
2994:
2966:
2956:
2927:
2917:
2885:
2875:
2844:
2814:
2807:
2795:
2766:
2756:
2728:
2718:
2689:
2679:
2654:
2644:
2617:
2469:"Welcome to The Chemistry Place"
1731:Glycolysis and Gluconeogenesis
497:
36:
27:
3382:Imidazol-4-one-5-propionic acid
836:phosphoenolpyruvate carboxylase
760:
493:(at 25 Ā°C , 100 kPa).
3196:Ī²-Hydroxy Ī²-methylglutaryl-CoA
3151:Ī²-Hydroxy Ī²-methylbutyric acid
2549:
2537:
2504:
2486:
2461:
2412:
2361:
1:
3411:1-Pyrroline-5-carboxylic acid
3156:Ī²-Hydroxy Ī²-methylbutyryl-CoA
2322:
999:by the actions of the enzyme
966:
600:
3541:2-Methyl-3-oxopropanoic acid
2446:10.1016/0014-5793(91)80944-X
2388:10.1371/journal.pone.0055549
7:
3809:Citric acid cycle compounds
3719:4-Hydroxyphenylpyruvic acid
3252:2-Aminomuconic semialdehyde
2295:
991:. In the cytosol there are
724:is catalyzed by the enzyme
10:
3850:
3595:generation of homocysteine
2345:Principles of Biochemistry
404:132.07 g/mol
3774:
3767:
3741:
3704:
3694:
3671:
3652:
3583:
3549:
3505:
3490:
3458:
3419:
3400:
3366:
3351:
3283:
3274:
3242:3-Hydroxyanthranilic acid
3204:
3140:
3086:
3073:
2840:
2813:
2806:
2633:
2607:
2602:
2312:Oxidative phosphorylation
1761:
1154:
1103:oxaloacetate and pyruvate
872:. It is also involved in
722:Keto-enol tautomerization
487:
428:
369:
349:
324:
75:
61:
49:
44:
35:
26:
3729:4-Maleylacetoacetic acid
3536:3-Hydroxyisobutyric acid
3392:Glutamate-1-semialdehyde
931:reduces oxaloacetate to
748:Oxaloacetate tautomerase
726:oxaloacetate tautomerase
3829:Metabolic intermediates
3575:2-Methylacetoacetyl-CoA
3531:3-Hydroxyisobutyryl-CoA
3067:metabolic intermediates
2494:"fatty acids synthesis"
2473:www.pearsonhighered.com
1148:Interactive pathway map
860:, where it reacts with
782:succinate dehydrogenase
3784:Cysteine sulfinic acid
3630:conversion to cysteine
3387:Formiminoglutamic acid
3314:3-Phosphoglyceric acid
3191:Ī²-Methylglutaconyl-CoA
2242:
1846:
1712:
1250:
1117:
1051:utilizing the enzymes
1027:
961:guanosine triphosphate
757:
571:metabolic intermediate
3516:Ī±-Ketoisovaleric acid
3171:Ī²-Ketoisocaproic acid
3166:Ī±-Ketoisocaproic acid
2775:CoA + ATP (GTP)
2241:
1845:
1711:
1249:
1133:O ā oxalate + acetate
1115:
1043:pathway occurring in
1025:
957:2-phosphoenolpyruvate
852:Biochemical functions
746:
736:is the substrate for
55:2-Oxobutanedioic acid
3603:-Adenosyl methionine
3186:Ī²-Methylcrotonyl-CoA
3176:Ī²-Ketoisocaproyl-CoA
3132:Ī²-Hydroxybutyryl-CoA
2248:|alt=TCACycle_WP78
1121:Oxalate biosynthesis
1097:Amino acid synthesis
1067:Fatty acid synthesis
921:pyruvate carboxylase
913:mitochondrial matrix
890:fatty acid synthesis
886:amino acid synthesis
844:or de- amination of
778:malate dehydrogenase
591:fatty acid synthesis
587:amino acid synthesis
51:Preferred IUPAC name
3776:Cysteine metabolism
3565:2-Methylbutyryl-CoA
3257:2-Aminomuconic acid
3237:3-Hydroxykynurenine
2437:1991FEBSL.286...76P
1073:fatty acid synthase
832:phosphoenolpyruvate
542:) is a crystalline
23:
3814:Dicarboxylic acids
3663:Ī±-Ketobutyric acid
3640:Ī±-Ketobutyric acid
3478:Ī³-Glutamylcysteine
3222:ā²-Formylkynurenine
3107:Ī±-Aminoadipic acid
2525:on 21 October 2013
2516:faculty.ksu.edu.sa
2302:Dioxosuccinic acid
2243:
1847:
1713:
1251:
1118:
1028:
758:
520:Infobox references
361:O=C(O)C(=O)CC(=O)O
68:2-Oxosuccinic acid
21:
3796:
3795:
3792:
3791:
3763:
3762:
3737:
3736:
3724:Homogentisic acid
3690:
3689:
3682:Methylmalonyl-CoA
3486:
3485:
3347:
3346:
3270:
3269:
3027:
3026:
3022:
3021:
2782:+ ADP (GDP)
2596:metabolic pathway
2593:Citric acid cycle
2544:Gadd, Geoffrey M.
2317:Citric acid cycle
2293:
2292:
858:citric acid cycle
826:Occurring in the
773:
756:isoform is shown.
595:citric acid cycle
528:Chemical compound
526:
525:
293:CompTox Dashboard
117:Interactive image
70:Ketosuccinic acid
22:Oxaloacetic acid
3841:
3819:Alpha-keto acids
3772:
3771:
3702:
3701:
3616:
3615:
3503:
3502:
3364:
3363:
3296:
3295:
3281:
3280:
3232:Anthranilic acid
3112:2-Oxoadipic acid
3084:
3083:
3054:
3047:
3040:
3031:
3030:
3008:
2998:
2970:
2960:
2950:
2931:
2921:
2909:
2889:
2879:
2870:
2848:
2818:
2811:
2799:
2770:
2760:
2732:
2722:
2693:
2683:
2658:
2648:
2631:
2621:
2605:
2604:
2586:
2579:
2572:
2563:
2562:
2556:
2553:
2547:
2541:
2535:
2534:
2532:
2530:
2524:
2518:. Archived from
2508:
2502:
2501:
2490:
2484:
2483:
2481:
2479:
2465:
2459:
2458:
2448:
2416:
2410:
2409:
2400:
2390:
2371:Escherichia coli
2365:
2359:
2358:
2340:
2284:
2283:
2275:
2168:
2163:
2158:
2153:
2148:
2143:
2138:
2133:
2128:
2123:
2118:
2113:
2108:
2103:
2098:
2093:
2088:
2083:
2078:
2073:
2068:
2063:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2023:
2018:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1978:
1973:
1968:
1963:
1958:
1953:
1948:
1943:
1938:
1933:
1928:
1923:
1918:
1913:
1908:
1903:
1898:
1893:
1888:
1883:
1878:
1873:
1868:
1863:
1858:
1853:
1754:
1753:
1745:
1627:
1622:
1617:
1612:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1547:
1542:
1537:
1532:
1527:
1522:
1517:
1512:
1507:
1502:
1497:
1492:
1487:
1482:
1477:
1472:
1467:
1462:
1457:
1452:
1447:
1442:
1437:
1432:
1427:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1387:
1382:
1377:
1372:
1367:
1362:
1357:
1352:
1347:
1342:
1337:
1332:
1327:
1322:
1317:
1312:
1307:
1302:
1297:
1292:
1287:
1282:
1277:
1272:
1267:
1262:
1257:
1152:
1151:
1129:oxaloacetate + H
1061:glyoxylate cycle
1053:isocitrate lyase
1037:glyoxylate cycle
1031:Glyoxylate cycle
882:glyoxylate cycle
870:citrate synthase
771:
583:glyoxylate cycle
548:chemical formula
544:organic compound
532:Oxaloacetic acid
510:
504:
501:
500:
483:-1205.58 kJ/mol
479:
452:
429:Thermochemistry
377:Chemical formula
317:
316:
301:
299:
283:
263:
252:
238:
218:
189:
181:
170:
159:
139:
119:
95:
64:Oxaloacetic acid
40:
31:
24:
20:
16:Organic compound
3849:
3848:
3844:
3843:
3842:
3840:
3839:
3838:
3824:Beta-keto acids
3799:
3798:
3797:
3788:
3759:
3733:
3686:
3667:
3648:
3613:
3612:
3579:
3545:
3526:Methacrylyl-CoA
3496:
3482:
3454:
3415:
3396:
3359:Ī±-ketoglutarate
3357:
3343:
3334:Phosphocreatine
3303:
3289:
3266:
3200:
3136:
3069:
3058:
3028:
3023:
3018:
3017:
3016:
3009:
3001:
3000:
2999:
2991:
2990:
2989:
2984:
2979:
2978:
2971:
2963:
2962:
2961:
2953:
2952:
2948:
2945:
2940:
2939:
2932:
2924:
2923:
2922:
2914:
2913:
2910:
2907:
2903:
2899:
2898:
2890:
2882:
2881:
2880:
2872:
2871:
2868:
2864:
2862:
2857:
2856:
2849:
2824:
2802:
2801:
2800:
2793:
2785:
2784:
2783:
2781:
2776:
2772:
2771:
2762:
2761:
2754:
2746:
2745:
2744:
2741:
2740:
2734:
2733:
2724:
2723:
2716:
2708:
2707:
2706:
2704:
2699:
2695:
2694:
2685:
2684:
2677:
2669:
2668:
2667:
2664:
2660:
2659:
2650:
2649:
2642:
2629:
2625:
2623:
2622:
2615:
2598:
2590:
2560:
2559:
2554:
2550:
2542:
2538:
2528:
2526:
2522:
2510:
2509:
2505:
2492:
2491:
2487:
2477:
2475:
2467:
2466:
2462:
2417:
2413:
2366:
2362:
2355:
2341:
2330:
2325:
2298:
2289:
2288:
2287:
2280:"TCACycle_WP78"
2278:
2276:
2272:
2267:
2266:
2265:
2261:TCACycle_WP78
2260:
2255:
2254:
2253:
2247:
2246:
2245:
2244:
2240:
2170:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2126:
2124:
2121:
2119:
2116:
2114:
2111:
2109:
2106:
2104:
2101:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2079:
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2056:
2054:
2051:
2049:
2046:
2044:
2041:
2039:
2036:
2034:
2031:
2029:
2026:
2024:
2021:
2019:
2016:
2014:
2011:
2009:
2006:
2004:
2001:
1999:
1996:
1994:
1991:
1989:
1986:
1984:
1981:
1979:
1976:
1974:
1971:
1969:
1966:
1964:
1961:
1959:
1956:
1954:
1951:
1949:
1946:
1944:
1941:
1939:
1936:
1934:
1931:
1929:
1926:
1924:
1921:
1919:
1916:
1914:
1911:
1909:
1906:
1904:
1901:
1899:
1896:
1894:
1891:
1889:
1886:
1884:
1881:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1856:
1854:
1851:
1848:
1844:
1759:
1758:
1757:
1748:
1746:
1742:
1737:
1736:
1735:
1730:
1725:
1724:
1723:
1717:
1716:
1715:
1714:
1710:
1629:
1628:
1625:
1623:
1620:
1618:
1615:
1613:
1610:
1608:
1605:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1568:
1565:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1425:
1423:
1420:
1418:
1415:
1413:
1410:
1408:
1405:
1403:
1400:
1398:
1395:
1393:
1390:
1388:
1385:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1353:
1350:
1348:
1345:
1343:
1340:
1338:
1335:
1333:
1330:
1328:
1325:
1323:
1320:
1318:
1315:
1313:
1310:
1308:
1305:
1303:
1300:
1298:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1275:
1273:
1270:
1268:
1265:
1263:
1260:
1258:
1255:
1252:
1248:
1150:
1132:
1123:
1099:
1091:
1087:
1069:
1057:malate synthase
1033:
1019:into the cell.
969:
905:Gluconeogenesis
902:
900:Gluconeogenesis
874:gluconeogenesis
868:, catalyzed by
854:
839:
834:, catalysed by
821:
817:
813:
809:
805:
801:
785:
776:, catalyzed by
763:
711:
707:
703:
699:
695:
691:
675:
671:
667:
663:
659:
655:
651:
644:
640:
636:
632:
628:
624:
620:
603:
575:gluconeogenesis
561:
557:
553:
536:oxalacetic acid
534:(also known as
529:
522:
517:
516:
515: ?)
506:
502:
498:
494:
480:
477:
471:
467:
464:
463:Std enthalpy of
456:-943.21 kJ/mol
453:
450:
444:
440:
437:
436:Std enthalpy of
393:
389:
385:
379:
365:
362:
357:
356:
345:
342:
341:
338:
332:
331:
320:
302:
295:
286:
266:
253:
241:
221:
208:
199:
162:
142:
122:
109:
98:
85:
71:
69:
67:
66:Oxalacetic acid
65:
57:
56:
17:
12:
11:
5:
3847:
3837:
3836:
3831:
3826:
3821:
3816:
3811:
3794:
3793:
3790:
3789:
3787:
3786:
3780:
3778:
3769:
3765:
3764:
3761:
3760:
3758:
3757:
3748:
3746:
3739:
3738:
3735:
3734:
3732:
3731:
3726:
3721:
3715:
3713:
3699:
3692:
3691:
3688:
3687:
3685:
3684:
3678:
3676:
3669:
3668:
3666:
3665:
3659:
3657:
3650:
3649:
3647:
3646:
3637:
3625:
3624:
3619:
3605:
3590:
3588:
3581:
3580:
3578:
3577:
3572:
3567:
3562:
3556:
3554:
3547:
3546:
3544:
3543:
3538:
3533:
3528:
3523:
3521:Isobutyryl-CoA
3518:
3512:
3510:
3500:
3488:
3487:
3484:
3483:
3481:
3480:
3462:
3460:
3456:
3455:
3453:
3452:
3447:
3442:
3437:
3432:
3426:
3424:
3417:
3416:
3414:
3413:
3407:
3405:
3398:
3397:
3395:
3394:
3389:
3384:
3379:
3373:
3371:
3361:
3349:
3348:
3345:
3344:
3342:
3341:
3336:
3331:
3317:
3316:
3310:
3308:
3293:
3278:
3272:
3271:
3268:
3267:
3265:
3264:
3259:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3215:
3213:
3202:
3201:
3199:
3198:
3193:
3188:
3183:
3178:
3173:
3168:
3163:
3161:Isovaleryl-CoA
3158:
3153:
3147:
3145:
3138:
3137:
3135:
3134:
3129:
3124:
3122:Glutaconyl-CoA
3119:
3114:
3109:
3104:
3099:
3093:
3091:
3081:
3071:
3070:
3057:
3056:
3049:
3042:
3034:
3025:
3024:
3020:
3019:
3013:2-oxoglutarate
3010:
3003:
3002:
2993:
2992:
2987:
2985:
2982:
2981:
2980:
2975:Oxalosuccinate
2972:
2965:
2964:
2955:
2954:
2946:
2943:
2942:
2941:
2933:
2926:
2925:
2916:
2915:
2911:
2905:
2902:
2901:
2900:
2891:
2884:
2883:
2874:
2873:
2866:
2863:
2860:
2859:
2858:
2850:
2843:
2842:
2841:
2839:
2836:
2835:
2832:
2826:
2825:
2822:
2819:
2812:
2804:
2803:
2794:
2787:
2786:
2779:
2777:
2774:
2773:
2765:
2764:
2763:
2755:
2748:
2747:
2742:
2738:
2736:
2735:
2727:
2726:
2725:
2717:
2710:
2709:
2702:
2700:
2697:
2696:
2688:
2687:
2686:
2678:
2671:
2670:
2665:
2662:
2661:
2653:
2652:
2651:
2643:
2636:
2635:
2634:
2632:
2627:
2616:
2609:
2608:
2603:
2600:
2599:
2589:
2588:
2581:
2574:
2566:
2558:
2557:
2548:
2536:
2503:
2485:
2460:
2431:(1ā2): 76ā78.
2411:
2360:
2353:
2327:
2326:
2324:
2321:
2320:
2319:
2314:
2309:
2304:
2297:
2294:
2291:
2290:
2286:
2285:
2269:
2268:
2257:
2256:
2171:
1849:
1775:
1774:
1773:
1772:
1770:
1769:
1768:
1767:
1766:
1765:
1760:
1756:
1755:
1739:
1738:
1727:
1726:
1630:
1253:
1168:
1167:
1166:
1165:
1163:
1162:
1161:
1160:
1159:
1158:
1149:
1146:
1135:
1134:
1130:
1122:
1119:
1098:
1095:
1094:
1093:
1092:+ malonyl-CoA
1089:
1085:
1068:
1065:
1032:
1029:
968:
965:
949:phosphorylated
945:decarboxylated
939:. Once in the
901:
898:
853:
850:
824:
823:
819:
815:
811:
810:+ ATP ā O
807:
803:
799:
762:
759:
714:
713:
709:
705:
701:
697:
693:
689:
678:
677:
673:
669:
665:
661:
657:
653:
649:
646:
642:
638:
634:
630:
626:
622:
618:
607:deprotonations
602:
599:
564:conjugate base
559:
555:
551:
527:
524:
523:
518:
496:
495:
491:standard state
488:
485:
484:
481:
475:
469:
461:
458:
457:
454:
448:
442:
434:
431:
430:
426:
425:
422:
416:
415:
412:
406:
405:
402:
396:
395:
391:
387:
383:
380:
375:
372:
371:
367:
366:
364:
363:
360:
352:
351:
350:
347:
346:
344:
343:
339:
336:
335:
327:
326:
325:
322:
321:
319:
318:
305:
303:
291:
288:
287:
285:
284:
276:
274:
268:
267:
265:
264:
256:
254:
246:
243:
242:
240:
239:
231:
229:
223:
222:
220:
219:
211:
209:
204:
201:
200:
198:
197:
193:
191:
183:
182:
172:
164:
163:
161:
160:
152:
150:
144:
143:
141:
140:
132:
130:
124:
123:
121:
120:
112:
110:
103:
100:
99:
97:
96:
88:
86:
81:
78:
77:
73:
72:
63:
59:
58:
54:
53:
47:
46:
42:
41:
33:
32:
15:
9:
6:
4:
3:
2:
3846:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3806:
3804:
3785:
3782:
3781:
3779:
3777:
3773:
3770:
3766:
3756:
3755:
3750:
3749:
3747:
3745:
3740:
3730:
3727:
3725:
3722:
3720:
3717:
3716:
3714:
3711:
3707:
3706:phenylalanine
3703:
3700:
3698:
3693:
3683:
3680:
3679:
3677:
3674:
3673:propionyl-CoA
3670:
3664:
3661:
3660:
3658:
3655:
3651:
3645:
3641:
3638:
3636:
3635:Cystathionine
3633:
3631:
3627:
3626:
3623:
3620:
3618:
3617:-homocysteine
3610:
3606:
3604:
3602:
3598:
3596:
3592:
3591:
3589:
3586:
3582:
3576:
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3557:
3555:
3552:
3548:
3542:
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3513:
3511:
3508:
3504:
3501:
3499:
3494:
3493:propionyl-CoA
3489:
3479:
3475:
3471:
3467:
3464:
3463:
3461:
3457:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3427:
3425:
3422:
3418:
3412:
3409:
3408:
3406:
3403:
3399:
3393:
3390:
3388:
3385:
3383:
3380:
3378:
3377:Urocanic acid
3375:
3374:
3372:
3369:
3365:
3362:
3360:
3355:
3350:
3340:
3337:
3335:
3332:
3330:
3326:
3322:
3319:
3318:
3315:
3312:
3311:
3309:
3306:
3301:
3297:
3294:
3292:
3287:
3282:
3279:
3277:
3273:
3263:
3260:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3221:
3217:
3216:
3214:
3211:
3207:
3203:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3148:
3146:
3143:
3139:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3094:
3092:
3089:
3085:
3082:
3080:
3076:
3072:
3068:
3065:
3062:
3055:
3050:
3048:
3043:
3041:
3036:
3035:
3032:
3015:
3014:
3007:
2997:
2977:
2976:
2969:
2959:
2938:
2937:
2930:
2920:
2897:
2896:
2888:
2878:
2855:
2854:
2847:
2838:
2837:
2833:
2831:
2828:
2827:
2821:NADH + H + CO
2820:
2817:
2810:
2805:
2798:
2792:
2791:
2769:
2759:
2753:
2752:
2731:
2721:
2715:
2714:
2692:
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2676:
2675:
2657:
2647:
2641:
2640:
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2587:
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2513:
2507:
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2434:
2430:
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2404:
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2376:
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2354:0-7167-4339-6
2350:
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2335:
2333:
2328:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2299:
2281:
2274:
2270:
2264:
2259:
2251:
2175:
1779:
1764:
1751:
1744:
1740:
1734:
1729:
1721:
1634:
1172:
1157:
1153:
1145:
1143:
1140:
1128:
1127:
1126:
1114:
1110:
1108:
1104:
1083:
1082:
1081:
1077:
1074:
1064:
1062:
1058:
1054:
1050:
1046:
1042:
1038:
1024:
1020:
1018:
1014:
1011:prefer these
1010:
1009:transaminases
1006:
1002:
998:
994:
990:
986:
982:
978:
974:
964:
962:
958:
954:
950:
946:
942:
938:
934:
930:
926:
922:
918:
914:
910:
906:
897:
895:
891:
887:
883:
879:
875:
871:
867:
863:
859:
849:
847:
846:aspartic acid
843:
837:
833:
829:
822:+ ADP + Pi
797:
796:
795:
793:
789:
783:
779:
775:
768:
755:
754:
749:
745:
741:
739:
735:
731:
727:
723:
719:
687:
686:
685:
683:
647:
616:
615:
614:
612:
608:
598:
596:
592:
588:
584:
580:
576:
572:
568:
565:
549:
545:
541:
537:
533:
521:
514:
509:
492:
486:
482:
474:
466:
460:
459:
455:
447:
439:
433:
432:
427:
423:
421:
420:Melting point
418:
417:
413:
411:
408:
407:
403:
401:
398:
397:
381:
378:
374:
373:
368:
359:
358:
355:
348:
334:
333:
330:
323:
315:
311:
310:DTXSID8021646
307:
306:
304:
294:
290:
289:
282:
278:
277:
275:
273:
270:
269:
262:
258:
257:
255:
249:
245:
244:
237:
233:
232:
230:
228:
225:
224:
217:
213:
212:
210:
207:
203:
202:
195:
194:
192:
190:
185:
184:
180:
176:
173:
171:
169:ECHA InfoCard
166:
165:
158:
154:
153:
151:
149:
146:
145:
138:
134:
133:
131:
129:
126:
125:
118:
114:
113:
111:
107:
102:
101:
94:
90:
89:
87:
84:
80:
79:
74:
60:
52:
48:
43:
39:
34:
30:
25:
19:
3834:Biomolecules
3751:
3744:oxaloacetate
3628:
3622:Homocysteine
3608:
3600:
3593:
3498:succinyl-CoA
3329:Glycocyamine
3262:Glutaryl-CoA
3219:
3127:Crotonyl-CoA
3117:Glutaryl-CoA
3097:Saccharopine
3011:
2973:
2934:
2892:
2851:
2790:Succinyl-CoA
2788:
2749:
2711:
2672:
2639:Oxaloacetate
2637:
2610:
2551:
2539:
2527:. Retrieved
2520:the original
2515:
2506:
2497:
2488:
2476:. Retrieved
2472:
2463:
2428:
2425:FEBS Letters
2424:
2414:
2378:
2374:
2370:
2363:
2344:
2273:
1762:
1743:
1155:
1142:oxaloacetase
1136:
1124:
1100:
1078:
1070:
1034:
989:oxaloacetate
988:
970:
955:and becomes
937:mitochondria
903:
855:
825:
764:
761:Biosynthesis
751:
729:
715:
679:
641:H + H, pK
609:to give the
604:
567:oxaloacetate
566:
539:
535:
531:
530:
472:
445:
76:Identifiers
62:Other names
18:
3474:glutathione
2498:www.rpi.edu
981:hepatocytes
370:Properties
175:100.005.755
137:CHEBI:30744
3803:Categories
3754:urea cycle
3611:-Adenosyl-
3585:methionine
3570:Tiglyl-CoA
3551:isoleucine
3450:Putrescine
3445:Cadaverine
3440:Citrulline
3339:Creatinine
3227:Kynurenine
3206:tryptophan
3079:acetyl-CoA
3064:metabolism
3061:Amino acid
2947:NAD(P)H +
2936:Isocitrate
2612:Acetyl-CoA
2529:21 October
2323:References
2307:Glycolysis
1013:keto acids
973:urea cycle
967:Urea cycle
894:complex II
878:urea cycle
862:acetyl-CoA
601:Properties
579:urea cycle
465:combustion
400:Molar mass
281:2F399MM81J
206:IUPHAR/BPS
148:ChemSpider
104:3D model (
83:CAS Number
3654:threonine
3470:glutamate
3435:Ornithine
3368:histidine
3354:glutamate
3181:Ī²-Leucine
2895:Aconitate
2751:Succinate
1107:glutamate
1005:aspartate
828:mesophyll
767:oxidation
708:+ H, pK
704:CC(O)CHCO
672:+ H, pK
546:with the
438:formation
414:1.6 g/cm
196:206-329-8
188:EC Number
3710:tyrosine
3697:fumarate
3644:Cysteine
3466:cysteine
3430:Agmatine
3421:arginine
3325:creatine
3286:pyruvate
3102:Allysine
2713:Fumarate
2407:23405168
2375:PLOS ONE
2296:See also
1049:bacteria
1041:anabolic
1017:nitrogen
1001:fumarase
993:fumarate
917:pyruvate
915:, where
864:to form
788:pyruvate
738:fumarase
734:tartrate
680:At high
660:H ā O
629:H ā O
593:and the
93:328-42-7
3402:proline
3321:glycine
3300:glycine
3291:citrate
3210:alanine
3142:leucine
2949:
2853:Citrate
2663:NADH +H
2478:5 April
2455:1864383
2433:Bibcode
2398:3565967
1771:[[File:
1164:[[File:
941:cytosol
909:glucose
866:citrate
774:-malate
712:= 13.03
692:CC(O)CH
664:CC(O)CH
652:CC(O)CH
633:CC(O)CH
621:CC(O)CH
611:dianion
569:, is a
554:CC(O)CH
513:what is
511: (
410:Density
394:
248:PubChem
3507:valine
3305:serine
3088:lysine
2983:
2944:NAD(P)
2912:
2861:
2698:
2674:Malate
2523:(PPTX)
2453:
2405:
2395:
2351:
1139:enzyme
1045:plants
997:malate
959:using
933:malate
888:, and
880:, the
876:, the
842:trans-
818:C(O)CO
802:C(O)CO
676:= 3.89
645:= 2.22
581:, the
577:, the
508:verify
505:
354:SMILES
236:C00036
45:Names
3768:Other
3459:other
1007:, as
806:+ HCO
730:trans
329:InChI
128:ChEBI
106:JSmol
3752:see
2893:cis-
2834:NAD
2737:FADH
2531:2013
2480:2018
2451:PMID
2403:PMID
2349:ISBN
2263:edit
2250:edit
1733:edit
1720:edit
1055:and
1047:and
1035:The
985:NADH
977:urea
971:The
947:and
929:NADH
718:enol
716:The
700:ā O
272:UNII
227:KEGG
216:5236
2830:CoA
2743:FAD
2666:NAD
2441:doi
2429:286
2393:PMC
2383:doi
2373:",
1084:HCO
951:by
925:ATP
838:.
814:CCH
792:ATP
769:of
753:(Z)
540:OAA
538:or
476:298
449:298
298:EPA
261:970
251:CID
157:945
3805::
3742:Gā
3695:Gā
3642:+
3491:Gā
3476::
3352:Gā
3327::
3288:ā
3284:Gā
2986:CO
2624:+
2514:.
2496:.
2471:.
2449:.
2439:.
2427:.
2423:.
2401:,
2391:,
2377:,
2331:^
2252:]]
1722:]]
896:.
884:,
848:.
798:CH
794::
740:.
728:.
696:CO
682:pH
668:CO
656:CO
637:CO
625:CO
617:HO
613::
597:.
589:,
585:,
558:CO
550:HO
468:(Ī
441:(Ī
3712:ā
3708:ā
3675:ā
3656:ā
3632::
3614:L
3609:S
3601:S
3597::
3587:ā
3553:ā
3509:ā
3495:ā
3472:ā
3468:+
3423:ā
3404:ā
3370:ā
3356:ā
3323:ā
3307:ā
3302:ā
3276:G
3220:N
3212:ā
3208:ā
3144:ā
3090:ā
3077:ā
3075:K
3053:e
3046:t
3039:v
2988:2
2951:H
2908:O
2906:2
2904:H
2869:O
2867:2
2865:H
2823:2
2780:i
2778:P
2739:2
2705:O
2703:2
2701:H
2630:O
2628:2
2626:H
2585:e
2578:t
2571:v
2533:.
2500:.
2482:.
2457:.
2443::
2435::
2385::
2379:8
2357:.
2282:.
2167:]
2162:]
2157:]
2152:]
2147:]
2142:]
2137:]
2132:]
2127:]
2122:]
2117:]
2112:]
2107:]
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2017:]
2012:]
2007:]
2002:]
1997:]
1992:]
1987:]
1982:]
1977:]
1972:]
1967:]
1962:]
1957:]
1952:]
1947:]
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1937:]
1932:]
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1752:.
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1511:]
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1471:]
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1416:]
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1406:]
1401:]
1396:]
1391:]
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1376:]
1371:]
1366:]
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1356:]
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1336:]
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1301:]
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1276:]
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1266:]
1261:]
1256:]
1131:2
1090:i
1086:3
820:2
816:2
812:2
808:3
804:2
800:3
772:L
710:a
706:2
702:2
698:2
694:2
690:2
688:O
674:a
670:2
666:2
662:2
658:2
654:2
650:2
648:O
643:a
639:2
635:2
631:2
627:2
623:2
619:2
560:2
556:2
552:2
503:Y
478:)
473:H
470:c
451:)
446:H
443:f
392:5
390:O
388:4
386:H
384:4
382:C
300:)
296:(
108:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
