317:
36:
751:
1023:
spectroscopy. Two of these anthocyanins, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside, predominated, comprising 24-40 and 49-58%, respectively, of the total anthocyanins in black raspberries. On the basis of both potency and concentration, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside were found to be the significant contributors to the antioxidant systems of black raspberries.
823:
27:
438:
602:. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent
1022:
Five anthocyanins were present in black raspberries: cyanidin 3-sambubioside, cyanidin 3-glucoside, cyanidin 3-xylosylrutinoside, cyanidin 3-rutinoside, and pelargonidin 3-rutinoside. Their identities and structures, with particular emphasis on cyanidin 3-xylosylrutinoside, were confirmed by NMR
797:
1810:
995:
Tulio AZ, Reese RN, Wyzgoski FJ, Rinaldi PL, Fu R, Scheerens JC, Miller AR (March 2008). "Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry".
451:
128:
788:
catalyses the aromatization and cyclization of the newly added carbonyl groups and facilitates the release of CoA. The compound then spontaneously cyclizes to form
366:
879:
Rahnasto-Rilla, M; Tyni, J; Huovinen, M; Jarho, E; Kulikowicz, T; Ravichandran, S; Bohr, V A; Ferrucci, L; Lahtela-Kakkonen, M; Moaddel, R (2018-03-07).
818:-Ketogluteratic acid, and anthocyanidin synthase. This compound spontaneously loses a water molecule and a hydroxide ion to form cyanidin (figure 3).
1676:
1136:
802:
Naringenin is then converted to cyanidin through several oxidizing and reducing steps. First naringenin is reacted with two equivalents of oxygen,
1087:
1689:
1919:
1901:
135:
1910:
1820:
1793:
1892:
1108:
Dewick, P. M. Medicinal
Natural Products: A Biosynthetic Approach, 3rd ed.; John Wiley and Sons, Ltd: United Kingdom 2009; pp 137-186
1887:
331:
1091:
945:
1702:
1715:
1663:
1752:
1739:
1616:
1598:
458:
1625:
1129:
781:
266:
1634:
1607:
1589:
1879:
757:
295:
1418:
1404:
676:
1462:
796:
1499:
1448:
1554:
1517:
1508:
1535:
1526:
1391:
822:
340:
InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
2008:
1382:
1122:
743:
700:
350:
InChI=1/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
2003:
1544:
1373:
769:
750:
780:
synthase and three malonyl CoA molecules to add six carbon atoms and three more keto groups ring through
175:
1458:
1414:
1095:
727:
704:
58:
48:
1265:
1163:
35:
1811:
delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)
1285:
1213:
892:
764:, a hydroxyl group is added to the para position of the aromatic ring. The compound then reacts with
712:
1949:
1038:"Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression"
312:
1806:
1776:
785:
739:
696:
86:
1959:
1114:
719:, which is necessary in the production of cyanidin, is synthesized through the shikimate pathway.
1939:
1943:
858:
1965:
1178:
1069:
1012:
974:
918:
811:
807:
731:
692:
1981:
1830:
699:(PKS) III. The shikimate pathway is a biosynthetic pathways that uses the starting materials
1444:
1059:
1049:
1004:
964:
954:
908:
900:
523:
394:
195:
282:
275:
96:
941:"Biological and catalytic functions of sirtuin 6 as targets for small-molecule modulators"
629:
623:
103:
896:
316:
155:
1975:
1970:
1193:
1064:
1037:
969:
913:
880:
429:
1997:
1343:
1231:
1203:
1145:
834:
716:
708:
651:
527:
1333:
1305:
1270:
1246:
1241:
1236:
1221:
1198:
1168:
659:
478:
255:
1954:
1844:
1581:
1479:
1320:
1275:
1188:
1183:
940:
615:
595:
535:
904:
1434:
1280:
1226:
1054:
959:
810:. The compound then reacts with NADPH and dihydroflavonol 4-reductase to form
789:
773:
765:
735:
723:
619:
575:
567:
559:
547:
417:
186:
738:. Prephenate undergoes dehydration, decarboxylation, and transamination with
1559:
1353:
1310:
1300:
1149:
838:
639:
603:
599:
583:
571:
563:
551:
531:
1073:
1016:
978:
922:
1036:
He F, Liang NN, Mu L, Pan QH, Wang J, Reeves MJ, Duan CQ (February 2012).
1295:
1290:
777:
680:
543:
214:
206:
760:(PAL) to form cinnamate. Through an oxidation with molecular oxygen and
756:
L-phenylalanine then undergoes an elimination of the primary amine with
1816:
579:
242:
1008:
1489:
1428:
772:
to attach CoA to the carboxylic acid group. The compound reacts with
665:
555:
539:
166:
428:
Except where otherwise noted, data are given for materials in their
26:
230:
1363:
761:
587:
146:
134:
127:
117:
591:
221:
1118:
63:
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1λ-benzopyran-1-ylium
859:"Cyanidin (E163a) – Overview, Uses, Side Effects & More"
300:
837:
studied, cyanidin most potently stimulated activity of the
806:-Ketogluteratic acid, and flavanone 3-hydroxylase to form
16:
Anthocyanidin pigment in flowering plant petals and fruits
691:
Cyanidin can be synthesized in berry plants through the
538:). It is a pigment found in many red berries including
446:
207:
1932:
1878:
1786:
1769:
1732:
1646:
1580:
1573:
1319:
1255:
1212:
1156:
254:
586:. It can also be found in other fruits such as
102:
95:
74:2-(3,4-Dihydroxyphenyl)chromenylium-3,5,7-triol
1779:(malvidin 3-(6″-malonylglucoside)-5-glucoside)
990:
988:
934:
932:
1130:
881:"Natural polyphenols as sirtuin 6 modulators"
711:, which then further reacts to form specific
8:
374:C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=2)O)O)O)O)O
1577:
1137:
1123:
1115:
997:Journal of Agricultural and Food Chemistry
469:
315:
194:
18:
1063:
1053:
968:
958:
912:
814:, which is further oxidized with oxygen,
281:
274:
850:
628:Cyanidin-3-xylosylrutinoside, found in
371:
336:
311:
722:In the synthesis of L-phenylalanine,
668:(cyanidin 3-O-galactoside), found in
343:Key: VEVZSMAEJFVWIL-UHFFFAOYSA-O
174:
154:
7:
1088:"Chalcone and Stilbene Biosynthesis"
746:to form L-phenylalanine (figure 1).
353:Key: VEVZSMAEJFVWIL-IKLDFBCSAG
245:
229:
1920:Epiafzelechin(4α→8)pelargonidin 3-
14:
1888:Malvidin glucoside-ethyl-catechin
1825:-coumaroylrutinoside)-5-glucoside
1787:Acylated anthocyanin diglycosides
52:3,3′,4′,5,7-Pentahydroxyflavylium
1902:Epicatechin(4α→8)pelargonidin 3-
821:
795:
749:
648:-β-glucoside, found in red onion
436:
379:Oc1ccc(cc1O)c3c2cc(O)cc(O)c2cc3O
34:
25:
1911:Afzelechin(4α→8)pelargonidin 3-
1802:-coumarylglucoside)-5-glucoside
1092:Queen Mary University of London
946:Journal of Biological Chemistry
432:(at 25 °C , 100 kPa).
1978:(degradation product of oenin)
526:. It is a particular type of
1:
1984:(oxidation product of malvin)
1893:Catechin(4α→8)pelargonidin 3-
861:. HealthKnight. 27 April 2022
638:-β-glucopyranoside, found in
1880:Flavanol-anthocyanin adducts
1847:(Delphinidin 3-rutinoside-7-
1324:(anthocyaninidin glycosides)
610:List of cyanidin derivatives
758:Phenylalanine ammonia-lyase
2025:
1647:Coumaroylated anthocyanins
1431:(Malvidin 3,5-diglucoside)
1259:-Methylated anthocyanidins
939:Klein MA, Denu JM (2020).
905:10.1038/s41598-018-22388-5
677:cyanidin-3,5-O-diglucoside
422:287.24 g/mol
1733:Caffeoylated anthocyanins
1555:Pulchellidin 3-rhamnoside
1055:10.3390/molecules17021571
960:10.1074/jbc.REV120.011438
472:
426:
387:
362:
327:
79:
69:
57:
47:
42:
33:
24:
1863:-glucosyl)oxybenzoyl)-β-
1770:Malonylated anthocyanins
1392:Pulchellidin 3-glucoside
1157:3-Hydroxyanthocyanidins
768:(CoA), CoA ligase, and
744:alpha-Ketoglutaric acid
701:Phosphoenolpyruvic acid
1859:-(4-hydroxybenzoyl)-β-
1621:-(6-acetyl)galactoside
1148:and their anthocyanin
658:-glucoside), found in
1574:Acylated anthocyanins
1214:3-Deoxyanthocyanidins
728:Claisen rearrangement
705:Erythrose 4-phosphate
59:Systematic IUPAC name
1724:-coumaroyl)glucoside
1711:-coumaroyl)glucoside
1698:-coumaroyl)glucoside
1685:-coumaroyl)glucoside
1672:-coumaroyl)glucoside
1639:-(6-acetyl)glucoside
1630:-(6-acetyl)glucoside
1612:-(6-acetyl)glucoside
1603:-(6-acetyl)glucoside
1594:-(6-acetyl)glucoside
713:aromatic amino acids
622:or 3-C-R), found in
1940:Metalloanthocyanins
1761:-caffeoyl)glucoside
1748:-caffeoyl)glucoside
1098:on 18 October 2015.
953:(32): 11021–11041.
897:2018NatSR...8.4163R
786:Aureusidin synthase
740:Pyridoxal phosphate
697:polyketide synthase
606:(SIRT6) activator.
21:
1966:Pyranoanthocyanins
1924:-β-glucopyranoside
1915:-β-glucopyranoside
1906:-β-glucopyranoside
1897:-β-glucopyranoside
1474:Others glycosides:
1437:(Pelargonidin 3,5-
459:Infobox references
19:
1991:
1990:
1874:
1873:
1866:
1862:
1841:-glucopyranoside)
1840:
1266:5-Desoxy-malvidin
1179:6-Hydroxycyanidin
1164:5-Desoxy-peonidin
1024:
1009:10.1021/jf072313k
812:leucopelargonidin
808:dihydrokaempferol
732:Chorismate mutase
693:shikimate pathway
634:Cyanidin-3,4′-di-
517:
516:
467:Chemical compound
465:
464:
296:CompTox Dashboard
136:Interactive image
129:Interactive image
2016:
1864:
1860:
1838:
1833:(petunidin 3--5-
1578:
1419:Delphinidin 3,5-
1336:(Pelargonidin 3-
1286:Kaempferidinidin
1139:
1132:
1125:
1116:
1109:
1106:
1100:
1099:
1094:. Archived from
1084:
1078:
1077:
1067:
1057:
1033:
1027:
1026:
1021:
992:
983:
982:
972:
962:
936:
927:
926:
916:
876:
870:
869:
867:
866:
855:
825:
799:
753:
534:version called
524:organic compound
482:
470:
449:
443:
440:
439:
395:Chemical formula
320:
319:
304:
302:
286: (chloride)
285:
278:
258:
247:
233:
209:
198:
178:
158:
138:
131:
107: (chloride)
106:
99:
38:
29:
22:
2024:
2023:
2019:
2018:
2017:
2015:
2014:
2013:
1994:
1993:
1992:
1987:
1928:
1870:
1821:Delphinidin 3-(
1782:
1765:
1728:
1648:
1642:
1569:
1562:(Delphinidin 3-
1356:(Delphinidin 3-
1323:
1315:
1251:
1208:
1152:
1143:
1113:
1112:
1107:
1103:
1086:
1085:
1081:
1048:(2): 1571–601.
1035:
1034:
1030:
994:
993:
986:
938:
937:
930:
878:
877:
873:
864:
862:
857:
856:
852:
847:
831:
734:enzyme to form
689:
630:black raspberry
624:black raspberry
612:
476:
468:
461:
456:
455:
454: ?)
445:
441:
437:
433:
411:
407:
403:
397:
383:
380:
375:
370:
369:
358:
355:
354:
351:
345:
344:
341:
335:
334:
323:
305:
298:
289:
261:
248:
236:
201:
181:
161:
141:
121:
110:
89:
75:
73:
65:
64:
53:
17:
12:
11:
5:
2022:
2020:
2012:
2011:
2009:Anthocyanidins
2006:
1996:
1995:
1989:
1988:
1986:
1985:
1979:
1976:Anthocyanone A
1973:
1971:Copigmentation
1968:
1963:
1957:
1952:
1950:Cyanosalvianin
1947:
1936:
1934:
1930:
1929:
1927:
1926:
1917:
1908:
1899:
1890:
1884:
1882:
1876:
1875:
1872:
1871:
1869:
1868:
1842:
1828:
1814:
1804:
1790:
1788:
1784:
1783:
1781:
1780:
1773:
1771:
1767:
1766:
1764:
1763:
1750:
1736:
1734:
1730:
1729:
1727:
1726:
1713:
1700:
1687:
1677:Delphinidin 3-
1674:
1660:
1658:
1644:
1643:
1641:
1632:
1623:
1614:
1605:
1599:Delphinidin 3-
1596:
1587:
1585:
1575:
1571:
1570:
1568:
1567:
1557:
1552:
1542:
1533:
1524:
1515:
1506:
1500:Delphinidin 3-
1497:
1487:
1471:
1470:
1463:Petunidin 3,5-
1456:
1442:
1432:
1426:
1412:
1395:
1394:
1389:
1380:
1371:
1361:
1351:
1341:
1327:
1325:
1317:
1316:
1314:
1313:
1308:
1303:
1298:
1293:
1288:
1283:
1278:
1273:
1268:
1262:
1260:
1253:
1252:
1250:
1249:
1244:
1239:
1234:
1229:
1224:
1218:
1216:
1210:
1209:
1207:
1206:
1201:
1196:
1194:Guibourtinidin
1191:
1186:
1181:
1176:
1171:
1166:
1160:
1158:
1154:
1153:
1146:Anthocyanidins
1144:
1142:
1141:
1134:
1127:
1119:
1111:
1110:
1101:
1079:
1028:
984:
928:
871:
849:
848:
846:
843:
835:anthocyanidins
830:
827:
688:
685:
684:
683:
673:
663:
649:
642:
632:
626:
611:
608:
515:
514:
509:
504:
498:
497:
492:
490:
484:
483:
466:
463:
462:
457:
435:
434:
430:standard state
427:
424:
423:
420:
414:
413:
409:
405:
401:
398:
393:
390:
389:
385:
384:
382:
381:
378:
376:
373:
365:
364:
363:
360:
359:
357:
356:
352:
349:
348:
346:
342:
339:
338:
330:
329:
328:
325:
324:
322:
321:
313:DTXSID10157933
308:
306:
294:
291:
290:
288:
287:
279:
271:
269:
263:
262:
260:
259:
251:
249:
241:
238:
237:
235:
234:
226:
224:
218:
217:
211:
203:
202:
200:
199:
191:
189:
183:
182:
180:
179:
171:
169:
163:
162:
160:
159:
151:
149:
143:
142:
140:
139:
132:
124:
122:
115:
112:
111:
109:
108:
100:
92:
90:
85:
82:
81:
77:
76:
71:
67:
66:
62:
61:
55:
54:
51:
45:
44:
40:
39:
31:
30:
15:
13:
10:
9:
6:
4:
3:
2:
2021:
2010:
2007:
2005:
2004:PH indicators
2002:
2001:
1999:
1983:
1980:
1977:
1974:
1972:
1969:
1967:
1964:
1961:
1958:
1956:
1953:
1951:
1948:
1945:
1941:
1938:
1937:
1935:
1933:Miscellaneous
1931:
1925:
1923:
1918:
1916:
1914:
1909:
1907:
1905:
1900:
1898:
1896:
1891:
1889:
1886:
1885:
1883:
1881:
1877:
1858:
1854:
1850:
1846:
1843:
1836:
1832:
1829:
1826:
1824:
1818:
1815:
1812:
1808:
1807:Gentiodelphin
1805:
1803:
1801:
1797:
1792:
1791:
1789:
1785:
1778:
1777:Malonylmalvin
1775:
1774:
1772:
1768:
1762:
1760:
1756:
1751:
1749:
1747:
1743:
1738:
1737:
1735:
1731:
1725:
1723:
1719:
1714:
1712:
1710:
1706:
1701:
1699:
1697:
1693:
1688:
1686:
1684:
1680:
1675:
1673:
1671:
1667:
1662:
1661:
1659:
1656:
1652:
1645:
1640:
1638:
1633:
1631:
1629:
1624:
1622:
1620:
1615:
1613:
1611:
1606:
1604:
1602:
1597:
1595:
1593:
1588:
1586:
1583:
1579:
1576:
1572:
1565:
1561:
1558:
1556:
1553:
1551:-galactoside)
1550:
1546:
1543:
1541:
1539:
1534:
1532:
1530:
1525:
1523:
1521:
1516:
1514:
1512:
1507:
1505:
1503:
1498:
1496:-galactoside)
1495:
1491:
1488:
1485:
1481:
1478:
1477:
1476:
1475:
1468:
1466:
1460:
1457:
1454:
1452:
1449:Peonidin 3,5-
1446:
1443:
1441:-diglucoside)
1440:
1436:
1433:
1430:
1427:
1424:
1422:
1416:
1413:
1410:
1408:
1405:Cyanidin 3,5-
1402:
1401:
1400:
1399:
1398:Diglucosides:
1393:
1390:
1388:
1386:
1381:
1379:
1377:
1372:
1369:
1365:
1362:
1359:
1355:
1352:
1349:
1345:
1344:Chrysanthemin
1342:
1339:
1335:
1332:
1331:
1330:
1326:
1322:
1318:
1312:
1309:
1307:
1304:
1302:
1299:
1297:
1294:
1292:
1289:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1267:
1264:
1263:
1261:
1258:
1254:
1248:
1245:
1243:
1240:
1238:
1235:
1233:
1232:Diosmetinidin
1230:
1228:
1225:
1223:
1220:
1219:
1217:
1215:
1211:
1205:
1204:Robinetinidin
1202:
1200:
1197:
1195:
1192:
1190:
1187:
1185:
1182:
1180:
1177:
1175:
1172:
1170:
1167:
1165:
1162:
1161:
1159:
1155:
1151:
1147:
1140:
1135:
1133:
1128:
1126:
1121:
1120:
1117:
1105:
1102:
1097:
1093:
1089:
1083:
1080:
1075:
1071:
1066:
1061:
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1051:
1047:
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1006:
1003:(6): 1880–8.
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948:
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747:
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733:
729:
725:
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718:
717:phenylalanine
714:
710:
709:shikimic acid
706:
702:
698:
694:
686:
682:
678:
674:
671:
667:
664:
661:
657:
653:
652:Chrysanthemin
650:
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621:
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569:
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541:
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529:
528:anthocyanidin
525:
522:is a natural
521:
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56:
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32:
28:
23:
1960:Protodelphin
1921:
1912:
1903:
1894:
1856:
1852:
1848:
1834:
1822:
1799:
1795:
1758:
1754:
1745:
1741:
1721:
1717:
1708:
1704:
1703:Petunidin 3-
1695:
1691:
1682:
1678:
1669:
1665:
1654:
1650:
1636:
1627:
1626:Petunidin 3-
1618:
1617:Petunidin 3-
1609:
1600:
1591:
1584:anthocyanins
1566:-rutinoside)
1563:
1548:
1547:(Malvidin 3-
1537:
1536:Petunidin 3-
1528:
1527:Petunidin 3-
1522:-galactoside
1519:
1518:Petunidin 3-
1513:-arabinoside
1510:
1509:Petunidin 3-
1501:
1493:
1492:(Cyanidin 3-
1486:-rutinoside)
1483:
1482:(Cyanidin 3-
1473:
1472:
1467:-diglucoside
1464:
1453:-diglucoside
1450:
1438:
1423:-diglucoside
1420:
1409:-diglucoside
1406:
1397:
1396:
1384:
1383:Petunidin 3-
1375:
1367:
1366:(Malvidin 3-
1357:
1347:
1346:(Cyanidin 3-
1337:
1334:Callistephin
1328:
1321:Anthocyanins
1306:Pulchellidin
1271:Capensinidin
1256:
1247:Tricetinidin
1242:Luteolinidin
1222:Apigeninidin
1199:Pelargonidin
1173:
1169:Aurantinidin
1104:
1096:the original
1082:
1045:
1041:
1031:
1020:
1000:
996:
950:
944:
888:
884:
874:
863:. Retrieved
853:
832:
820:
815:
803:
801:
794:
792:(figure 2).
755:
748:
726:undergoes a
721:
690:
687:Biosynthesis
679:), found in
669:
660:blackcurrant
655:
654:(cyanidin-3-
645:
644:Cyanidin-4′-
635:
618:(cyanidin-3-
536:anthocyanins
519:
518:
511:
506:
501:
494:
487:
479:pH indicator
473:
176:ChEMBL404515
80:Identifiers
70:Other names
1955:Protocyanin
1867:-glucoside)
1845:Violdelphin
1794:Cyanidin 3-
1753:Peonidin 3-
1740:Malvidin 3-
1716:Peonidin 3-
1690:Malvidin 3-
1664:Cyanidin 3-
1635:Peonidin 3-
1608:Malvidin 3-
1590:Cyanidin 3-
1540:-rutinoside
1531:-rhamnoside
1504:-rhamnoside
1480:Antirrhinin
1374:Peonidin 3-
1370:-glucoside)
1360:-glucoside)
1350:-glucoside)
1340:-glucoside)
1329:Glucosides:
1276:Europinidin
1189:Fisetinidin
1184:Delphinidin
891:(1): 4163.
833:Among many
616:Antirrhinin
596:red cabbage
495:above pH 11
388:Properties
156:CHEBI:27843
1998:Categories
1944:commelinin
1582:Acetylated
1435:Pelargonin
1387:-glucoside
1378:-glucoside
1281:Hirsutidin
1237:Gesneridin
1227:Columnidin
1150:glucosides
865:2022-04-30
845:References
829:Activation
790:naringenin
774:naringenin
766:Coenzyme A
742:(PLP) and
736:prephenate
724:chorismate
703:(PEP) and
620:rutinoside
582:berry and
576:loganberry
568:elderberry
560:chokeberry
548:blackberry
488:below pH 3
418:Molar mass
283:2G4283G96U
276:7732ZHU564
187:ChemSpider
116:3D model (
97:13306-05-3
87:CAS Number
72:Cyanidine
49:IUPAC name
1560:Tulipanin
1354:Myrtillin
1311:Rosinidin
1301:Petunidin
1042:Molecules
839:sirtuin 6
670:Vaccinium
640:red onion
604:sirtuin 6
600:red onion
594:, and in
584:raspberry
564:cranberry
552:blueberry
532:glycoside
215:(colours)
20:Cyanidin
1545:Primulin
1403:Cyanin (
1296:Peonidin
1291:Malvidin
1174:Cyanidin
1074:22314380
1017:18290621
979:32518153
923:29515203
841:enzyme.
778:chalcone
707:to form
681:red wine
675:Cyanin (
572:hawthorn
544:bilberry
520:Cyanidin
474:Cyanidin
208:E number
104:528-58-5
1982:Malvone
1855:-(4-(6-
1831:Petanin
1817:Nasunin
1459:Petunin
1415:Delphin
1065:6268338
970:7415977
914:5841289
893:Bibcode
885:Sci Rep
782:PKS III
672:species
452:what is
450: (
412:
243:PubChem
1653:- and
1490:Ideain
1445:Peonin
1429:Malvin
1072:
1062:
1015:
977:
967:
921:
911:
666:Ideain
662:pomace
588:apples
556:cherry
540:grapes
447:verify
444:
367:SMILES
256:128861
231:C05905
213:E163a
196:114193
167:ChEMBL
43:Names
1798:-(di-
1655:trans
1364:Oenin
816:alpha
804:alpha
762:NADPH
730:by a
592:plums
332:InChI
147:ChEBI
118:JSmol
1851:-(6-
1757:-(6-
1744:-(6-
1720:-(6-
1707:-(6-
1694:-(6-
1681:-(6-
1668:-(6-
1070:PMID
1013:PMID
975:PMID
919:PMID
889:7, 8
715:. L-
695:and
598:and
590:and
580:açai
267:UNII
222:KEGG
1837:-β-
1651:cis
1060:PMC
1050:doi
1005:doi
965:PMC
955:doi
951:295
909:PMC
901:doi
770:ATP
301:EPA
246:CID
2000::
1657:-)
1090:.
1068:.
1058:.
1046:17
1044:.
1040:.
1019:.
1011:.
1001:56
999:.
987:^
973:.
963:.
949:.
943:.
931:^
917:.
907:.
899:.
887:.
883:.
784:.
578:,
574:,
570:,
566:,
562:,
558:,
554:,
550:,
546:,
542:,
512:11
406:11
402:15
1962:)
1946:)
1942:(
1922:O
1913:O
1904:O
1895:O
1865:D
1861:D
1857:O
1853:O
1849:O
1839:D
1835:O
1827:)
1823:p
1819:(
1813:)
1809:(
1800:p
1796:O
1759:p
1755:O
1746:p
1742:O
1722:p
1718:O
1709:p
1705:O
1696:p
1692:O
1683:p
1679:O
1670:p
1666:O
1649:(
1637:O
1628:O
1619:O
1610:O
1601:O
1592:O
1564:O
1549:O
1538:O
1529:O
1520:O
1511:O
1502:O
1494:O
1484:O
1469:)
1465:O
1461:(
1455:)
1451:O
1447:(
1439:O
1425:)
1421:O
1417:(
1411:)
1407:O
1385:O
1376:O
1368:O
1358:O
1348:O
1338:O
1257:O
1138:e
1131:t
1124:v
1076:.
1052::
1007::
981:.
957::
925:.
903::
895::
868:.
776:-
656:O
646:O
636:O
530:(
507:⇌
502:3
481:)
477:(
442:N
410:6
408:O
404:H
400:C
303:)
299:(
120:)
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