299:
190:
35:
26:
433:
604:
Paolo Cabras; Alberto
Angioni; Carlo Tuberoso; Ignazio Floris; Fabiano Reniero; Claude Guillou; Stefano Ghelli (1999). "Homogentisic Acid: A Phenolic Acid as a Marker of Strawberry-Tree (
892:
798:
Lindstedt, Sven; Odelhog, Birgit; Rundgren, Marianne (1977). "Purification and Some
Properties of 4-Hydroxyphenylpyruvate Dioxygenase from Pseudomonas sp. P.J. 814".
1016:
446:
885:
878:
348:
644:
1661:
1087:
441:
1400:
991:
1714:
996:
576:
479:
530:
313:
453:
1222:
223:
107:
1930:
1838:
1251:
580:
827:"The oxidation in liver of l-tyrosine to acetoacetate through p-hydroxyphenylpyruvate and homogentisic acid"
1381:
256:
185:
1925:
1654:
1559:
1092:
277:
1790:
1778:
1766:
1760:
1448:
1356:
1082:
1006:
1031:
1945:
1569:
1376:
1232:
1011:
716:
584:
294:
217:
1435:
1679:
1415:
1371:
1199:
972:
568:
870:
1940:
1935:
1825:
1647:
1624:
1503:
1480:
1318:
1227:
1154:
1059:
947:
907:
711:
550:
1639:
1470:
1806:
1752:
1692:
1687:
1440:
1116:
915:
904:
672:
265:
47:
8:
1784:
1616:
1405:
1097:
1077:
490:
147:
83:
73:
298:
189:
127:
1026:
851:
826:
603:
1522:
856:
780:
739:
734:
695:
625:
499:
495:
725:
693:
1072:
952:
846:
838:
807:
770:
729:
721:
664:
617:
371:
1811:
1366:
1174:
494:
where it is associated with the production of brown pigments. It is oxidatively
245:
1895:
1697:
1361:
1001:
962:
572:
424:
1919:
1900:
1890:
1885:
1869:
1772:
1733:
1670:
1546:
1513:
1475:
1333:
1217:
558:
514:
474:
469:
412:
178:
34:
478:(strawberry-tree) honey. It is also present in the bacterial plant pathogen
1584:
1462:
1338:
1169:
1102:
967:
957:
937:
860:
784:
743:
629:
538:
503:
1021:
1859:
1833:
1314:
775:
758:
811:
167:
1864:
1594:
1425:
1410:
1391:
1290:
1285:
1280:
1179:
1067:
1046:
919:
901:
554:
399:
138:
842:
621:
322:
InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
1494:
1310:
1275:
1208:
1194:
332:
InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
668:
423:
Except where otherwise noted, data are given for materials in their
25:
1854:
1550:
1537:
1484:
1306:
1270:
1261:
1165:
1126:
942:
562:
534:
206:
158:
106:
1242:
1161:
1140:
1131:
1050:
1036:
982:
900:
694:
Alexandra
Carreira; Luísa M. Ferreira; Virgílio Loureiro (2001).
232:
1669:
1347:
1145:
928:
525:
Accumulation of excess homogentisic acid and its oxide, named
118:
96:
700:
533:(typically due to a mutation) in the degradative pathway of
282:
417:
150 to 152 °C (302 to 306 °F; 423 to 425 K)
197:
757:
Phornphutkul C, Introne WJ, Perry MB, et al. (2002).
579:
to yield homogentisate. If active and present, the enzyme
797:
756:
502:, one of the main constituents of the 'blood sweat' of
1917:
244:
82:
1139:
824:
1655:
886:
642:
583:further degrades homogentisic acid to yield
750:
529:, is a result of the failure of the enzyme
1662:
1648:
893:
879:
297:
188:
146:
850:
774:
733:
715:
575:of tyrosine) is acted upon by the enzyme
264:
1799:
293:
222:
166:
1918:
825:Knox WE, LeMay-Knox M (October 1951).
468:(2,5-dihydroxyphenylacetic acid) is a
179:
1643:
1088:2-Amino-3-carboxymuconic semialdehyde
874:
325:Key: IGMNYECMUMZDDF-UHFFFAOYSA-N
126:
1401:2,3-Dihydroxy-3-methylpentanoic acid
577:4-hydroxyphenylpyruvate dioxygenase
335:Key: IGMNYECMUMZDDF-UHFFFAOYAK
235:
205:
13:
653:associated with homogentisic acid"
520:
14:
1957:
759:"Natural history of alkaptonuria"
531:homogentisic acid 1,2-dioxygenase
657:Canadian Journal of Microbiology
557:of aromatic amino acids such as
431:
383:
52:(2,5-Dihydroxyphenyl)acetic acid
33:
24:
1223:Imidazol-4-one-5-propionic acid
763:New England Journal of Medicine
726:10.1128/AEM.67.8.3463-3468.2001
544:
537:, consequently associated with
427:(at 25 °C , 100 kPa).
1839:Phloroglucinol carboxylic acid
1718:-Hydroxybenzoic acid glucoside
1037:β-Hydroxy β-methylglutaryl-CoA
992:β-Hydroxy β-methylbutyric acid
818:
791:
687:
643:Goodwin PH, Sopher CR (1994).
636:
597:
389:
377:
1:
1252:1-Pyrroline-5-carboxylic acid
997:β-Hydroxy β-methylbutyryl-CoA
590:
581:homogentisate 1,2-dioxygenase
509:It is less commonly known as
1673:(C6-C1) and their glycosides
1382:2-Methyl-3-oxopropanoic acid
696:"Brown Pigments Produced by
7:
1783:3,4-Dihydroxybenzoic acid (
1771:2,5-Dihydroxybenzoic acid (
1560:4-Hydroxyphenylpyruvic acid
1093:2-Aminomuconic semialdehyde
10:
1962:
1436:generation of homocysteine
1878:
1847:
1824:
1791:3,5-Dihydroxybenzoic acid
1779:2,6-Dihydroxybenzoic acid
1767:2,4-Dihydroxybenzoic acid
1761:2,3-Dihydroxybenzoic acid
1751:
1726:
1707:
1678:
1615:
1608:
1582:
1545:
1535:
1512:
1493:
1424:
1390:
1346:
1331:
1299:
1260:
1241:
1207:
1192:
1124:
1115:
1083:3-Hydroxyanthranilic acid
1045:
981:
927:
914:
421:
364:
344:
309:
66:
58:
46:
41:
32:
23:
1680:Monohydroxybenzoic acids
1570:4-Maleylacetoacetic acid
1377:3-Hydroxyisobutyric acid
1233:Glutamate-1-semialdehyde
585:4-maleylacetoacetic acid
488:as well as in the yeast
1826:Trihydroxybenzoic acids
1700:(2-Hydroxybenzoic acid)
1416:2-Methylacetoacetyl-CoA
1372:3-Hydroxyisobutyryl-CoA
908:metabolic intermediates
831:The Biochemical Journal
645:"Brown pigmentation of
569:4-Hydroxyphenylpyruvate
1753:Dihydroxybenzoic acids
1625:Cysteine sulfinic acid
1471:conversion to cysteine
1228:Formiminoglutamic acid
1155:3-Phosphoglyceric acid
1032:β-Methylglutaconyl-CoA
704:Appl Environ Microbiol
647:Xanthomonas campestris
481:Xanthomonas campestris
1931:Biochemical reactions
1807:Ethyl protocatechuate
1740:-hydroxybenzoic acid)
1693:4-Hydroxybenzoic acid
1688:3-Hydroxybenzoic acid
1357:α-Ketoisovaleric acid
1012:β-Ketoisocaproic acid
1007:α-Ketoisocaproic acid
513:, the name chosen by
1444:-Adenosyl methionine
1027:β-Methylcrotonyl-CoA
1017:β-Ketoisocaproyl-CoA
973:β-Hydroxybutyryl-CoA
776:10.1056/NEJMoa021736
48:Preferred IUPAC name
1785:Protocatechuic acid
1617:Cysteine metabolism
1406:2-Methylbutyryl-CoA
1098:2-Aminomuconic acid
1078:3-Hydroxykynurenine
812:10.1021/bi00634a013
698:Yarrowia lipolytica
610:J. Agric. Food Chem
491:Yarrowia lipolytica
407: g·mol
356:O=C(O)Cc1cc(O)ccc1O
20:
1926:Phenylacetic acids
1504:α-Ketobutyric acid
1481:α-Ketobutyric acid
1319:γ-Glutamylcysteine
1063:′-Formylkynurenine
948:α-Aminoadipic acid
454:Infobox references
19:Homogentisic acid
18:
1913:
1912:
1909:
1908:
1820:
1819:
1763:(Hypogallic acid)
1747:
1746:
1637:
1636:
1633:
1632:
1604:
1603:
1578:
1577:
1565:Homogentisic acid
1531:
1530:
1523:Methylmalonyl-CoA
1327:
1326:
1188:
1187:
1111:
1110:
843:10.1042/bj0490686
806:(15): 3369–3377.
622:10.1021/jf990141o
616:(10): 4064–4067.
500:hipposudoric acid
472:usually found in
466:Homogentisic acid
462:Chemical compound
460:
459:
278:CompTox Dashboard
224:Homogentisic+acid
108:Interactive image
1953:
1845:
1844:
1797:
1796:
1705:
1704:
1664:
1657:
1650:
1641:
1640:
1613:
1612:
1543:
1542:
1457:
1456:
1344:
1343:
1205:
1204:
1137:
1136:
1122:
1121:
1073:Anthranilic acid
953:2-Oxoadipic acid
925:
924:
895:
888:
881:
872:
871:
865:
864:
854:
822:
816:
815:
795:
789:
788:
778:
754:
748:
747:
737:
719:
710:(8): 3463–3468.
691:
685:
684:
682:
680:
671:. Archived from
640:
634:
633:
601:
444:
438:
435:
434:
406:
391:
385:
379:
372:Chemical formula
302:
301:
286:
284:
268:
248:
237:
226:
209:
192:
181:
170:
150:
130:
110:
86:
37:
28:
21:
17:
1961:
1960:
1956:
1955:
1954:
1952:
1951:
1950:
1946:Phenylethanoids
1916:
1915:
1914:
1905:
1874:
1843:
1816:
1812:Orsellinic acid
1795:
1743:
1722:
1703:
1674:
1668:
1638:
1629:
1600:
1574:
1527:
1508:
1489:
1454:
1453:
1420:
1386:
1367:Methacrylyl-CoA
1337:
1323:
1295:
1256:
1237:
1200:α-ketoglutarate
1198:
1184:
1175:Phosphocreatine
1144:
1130:
1107:
1041:
977:
910:
899:
869:
868:
823:
819:
796:
792:
769:(26): 2111–21.
755:
751:
692:
688:
678:
676:
675:on 21 July 2011
669:10.1139/m94-005
641:
637:
602:
598:
593:
547:
523:
521:Human pathology
463:
456:
451:
450:
449: ?)
440:
436:
432:
428:
404:
394:
388:
382:
374:
360:
357:
352:
351:
340:
337:
336:
333:
327:
326:
323:
317:
316:
305:
287:
280:
271:
251:
238:
212:
173:
153:
133:
113:
100:
89:
76:
62:
54:
53:
12:
11:
5:
1959:
1949:
1948:
1943:
1938:
1933:
1928:
1911:
1910:
1907:
1906:
1904:
1903:
1898:
1896:Methyl gallate
1893:
1888:
1882:
1880:
1876:
1875:
1873:
1872:
1867:
1862:
1857:
1851:
1849:
1842:
1841:
1836:
1830:
1828:
1822:
1821:
1818:
1817:
1815:
1814:
1809:
1803:
1801:
1794:
1793:
1788:
1781:
1776:
1769:
1764:
1757:
1755:
1749:
1748:
1745:
1744:
1742:
1741:
1730:
1728:
1724:
1723:
1721:
1720:
1711:
1709:
1702:
1701:
1698:Salicylic acid
1695:
1690:
1684:
1682:
1676:
1675:
1671:Phenolic acids
1667:
1666:
1659:
1652:
1644:
1635:
1634:
1631:
1630:
1628:
1627:
1621:
1619:
1610:
1606:
1605:
1602:
1601:
1599:
1598:
1589:
1587:
1580:
1579:
1576:
1575:
1573:
1572:
1567:
1562:
1556:
1554:
1540:
1533:
1532:
1529:
1528:
1526:
1525:
1519:
1517:
1510:
1509:
1507:
1506:
1500:
1498:
1491:
1490:
1488:
1487:
1478:
1466:
1465:
1460:
1446:
1431:
1429:
1422:
1421:
1419:
1418:
1413:
1408:
1403:
1397:
1395:
1388:
1387:
1385:
1384:
1379:
1374:
1369:
1364:
1362:Isobutyryl-CoA
1359:
1353:
1351:
1341:
1329:
1328:
1325:
1324:
1322:
1321:
1303:
1301:
1297:
1296:
1294:
1293:
1288:
1283:
1278:
1273:
1267:
1265:
1258:
1257:
1255:
1254:
1248:
1246:
1239:
1238:
1236:
1235:
1230:
1225:
1220:
1214:
1212:
1202:
1190:
1189:
1186:
1185:
1183:
1182:
1177:
1172:
1158:
1157:
1151:
1149:
1134:
1119:
1113:
1112:
1109:
1108:
1106:
1105:
1100:
1095:
1090:
1085:
1080:
1075:
1070:
1065:
1056:
1054:
1043:
1042:
1040:
1039:
1034:
1029:
1024:
1019:
1014:
1009:
1004:
1002:Isovaleryl-CoA
999:
994:
988:
986:
979:
978:
976:
975:
970:
965:
963:Glutaconyl-CoA
960:
955:
950:
945:
940:
934:
932:
922:
912:
911:
898:
897:
890:
883:
875:
867:
866:
817:
790:
749:
717:10.1.1.319.523
686:
635:
595:
594:
592:
589:
573:transamination
546:
543:
522:
519:
504:hippopotamuses
461:
458:
457:
452:
430:
429:
425:standard state
422:
419:
418:
415:
409:
408:
402:
396:
395:
392:
386:
380:
375:
370:
367:
366:
362:
361:
359:
358:
355:
347:
346:
345:
342:
341:
339:
338:
334:
331:
330:
328:
324:
321:
320:
312:
311:
310:
307:
306:
304:
303:
290:
288:
276:
273:
272:
270:
269:
261:
259:
253:
252:
250:
249:
241:
239:
231:
228:
227:
220:
214:
213:
211:
210:
202:
200:
194:
193:
183:
175:
174:
172:
171:
163:
161:
155:
154:
152:
151:
143:
141:
135:
134:
132:
131:
123:
121:
115:
114:
112:
111:
103:
101:
94:
91:
90:
88:
87:
79:
77:
72:
69:
68:
64:
63:
60:
56:
55:
51:
50:
44:
43:
39:
38:
30:
29:
9:
6:
4:
3:
2:
1958:
1947:
1944:
1942:
1941:Hydroxy acids
1939:
1937:
1936:Hydroquinones
1934:
1932:
1929:
1927:
1924:
1923:
1921:
1902:
1901:Syringic acid
1899:
1897:
1894:
1892:
1891:Eudesmic acid
1889:
1887:
1886:Ethyl gallate
1884:
1883:
1881:
1877:
1871:
1870:Chebulic acid
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1852:
1850:
1846:
1840:
1837:
1835:
1832:
1831:
1829:
1827:
1823:
1813:
1810:
1808:
1805:
1804:
1802:
1798:
1792:
1789:
1786:
1782:
1780:
1777:
1774:
1773:Gentisic acid
1770:
1768:
1765:
1762:
1759:
1758:
1756:
1754:
1750:
1739:
1735:
1734:Methylparaben
1732:
1731:
1729:
1725:
1719:
1717:
1713:
1712:
1710:
1706:
1699:
1696:
1694:
1691:
1689:
1686:
1685:
1683:
1681:
1677:
1672:
1665:
1660:
1658:
1653:
1651:
1646:
1645:
1642:
1626:
1623:
1622:
1620:
1618:
1614:
1611:
1607:
1597:
1596:
1591:
1590:
1588:
1586:
1581:
1571:
1568:
1566:
1563:
1561:
1558:
1557:
1555:
1552:
1548:
1547:phenylalanine
1544:
1541:
1539:
1534:
1524:
1521:
1520:
1518:
1515:
1514:propionyl-CoA
1511:
1505:
1502:
1501:
1499:
1496:
1492:
1486:
1482:
1479:
1477:
1476:Cystathionine
1474:
1472:
1468:
1467:
1464:
1461:
1459:
1458:-homocysteine
1451:
1447:
1445:
1443:
1439:
1437:
1433:
1432:
1430:
1427:
1423:
1417:
1414:
1412:
1409:
1407:
1404:
1402:
1399:
1398:
1396:
1393:
1389:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1354:
1352:
1349:
1345:
1342:
1340:
1335:
1334:propionyl-CoA
1330:
1320:
1316:
1312:
1308:
1305:
1304:
1302:
1298:
1292:
1289:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1268:
1266:
1263:
1259:
1253:
1250:
1249:
1247:
1244:
1240:
1234:
1231:
1229:
1226:
1224:
1221:
1219:
1218:Urocanic acid
1216:
1215:
1213:
1210:
1206:
1203:
1201:
1196:
1191:
1181:
1178:
1176:
1173:
1171:
1167:
1163:
1160:
1159:
1156:
1153:
1152:
1150:
1147:
1142:
1138:
1135:
1133:
1128:
1123:
1120:
1118:
1114:
1104:
1101:
1099:
1096:
1094:
1091:
1089:
1086:
1084:
1081:
1079:
1076:
1074:
1071:
1069:
1066:
1064:
1062:
1058:
1057:
1055:
1052:
1048:
1044:
1038:
1035:
1033:
1030:
1028:
1025:
1023:
1020:
1018:
1015:
1013:
1010:
1008:
1005:
1003:
1000:
998:
995:
993:
990:
989:
987:
984:
980:
974:
971:
969:
966:
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837:(5): 686–93.
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571:(produced by
570:
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559:phenylalanine
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515:William Prout
512:
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1715:
1592:
1585:oxaloacetate
1564:
1469:
1463:Homocysteine
1449:
1441:
1434:
1339:succinyl-CoA
1170:Glycocyamine
1103:Glutaryl-CoA
1060:
968:Crotonyl-CoA
958:Glutaryl-CoA
938:Saccharopine
834:
830:
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800:Biochemistry
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677:. Retrieved
673:the original
663:(1): 28–34.
660:
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567:
551:intermediate
548:
545:Intermediate
539:alkaptonuria
526:
524:
511:melanic acid
510:
508:
489:
484:
480:
473:
465:
464:
67:Identifiers
61:Melanic acid
59:Other names
15:
1860:Norbergenin
1834:Gallic acid
1315:glutathione
679:25 February
365:Properties
186:100.006.540
128:CHEBI:44747
1920:Categories
1865:Theogallin
1848:Glycosides
1708:Glycosides
1595:urea cycle
1452:-Adenosyl-
1426:methionine
1411:Tiglyl-CoA
1392:isoleucine
1291:Putrescine
1286:Cadaverine
1281:Citrulline
1180:Creatinine
1068:Kynurenine
1047:tryptophan
920:acetyl-CoA
905:metabolism
902:Amino acid
608:) Honey".
591:References
555:catabolism
400:Molar mass
266:NP8UE6VF08
139:ChemSpider
95:3D model (
74:CAS Number
1879:Alkylated
1800:Alkylated
1727:Alkylated
1495:threonine
1311:glutamate
1276:Ornithine
1209:histidine
1195:glutamate
1022:β-Leucine
712:CiteSeerX
549:It is an
496:dimerised
1855:Bergenin
1736:(Methyl-
1551:tyrosine
1538:fumarate
1485:Cysteine
1307:cysteine
1271:Agmatine
1262:arginine
1166:creatine
1127:pyruvate
943:Allysine
861:14886367
785:12501223
744:11472920
651:phaseoli
630:10552766
563:tyrosine
535:tyrosine
527:alkapton
498:to form
485:phaseoli
159:DrugBank
84:451-13-8
1243:proline
1162:glycine
1141:glycine
1132:citrate
1051:alanine
983:leucine
852:1197578
553:in the
447:what is
445: (
405:168.148
233:PubChem
168:DB08327
1348:valine
1146:serine
929:lysine
859:
849:
783:
742:
732:
714:
628:
442:verify
439:
349:SMILES
207:C00544
42:Names
1609:Other
1300:other
735:93044
314:InChI
119:ChEBI
97:JSmol
1593:see
857:PMID
781:PMID
740:PMID
681:2011
649:pv.
626:PMID
561:and
483:pv.
257:UNII
218:MeSH
198:KEGG
847:PMC
839:doi
808:doi
771:doi
767:347
730:PMC
722:doi
665:doi
618:doi
283:EPA
246:780
236:CID
148:759
1922::
1583:G→
1536:G→
1483:+
1332:G→
1317::
1193:G→
1168::
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1125:G→
855:.
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1787:)
1775:)
1738:p
1716:p
1663:e
1656:t
1649:v
1553:→
1549:→
1516:→
1497:→
1473::
1455:L
1450:S
1442:S
1438::
1428:→
1394:→
1350:→
1336:→
1313:→
1309:+
1264:→
1245:→
1211:→
1197:→
1164:→
1148:→
1143:→
1117:G
1061:N
1053:→
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985:→
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916:K
894:e
887:t
880:v
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841::
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773::
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683:.
667::
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620::
437:Y
393:4
390:O
387:8
384:H
381:8
378:C
285:)
281:(
99:)
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