221:
26:
337:
1054:
Patel, P.; Cossette, C.; Anumolu, J. R.; Gravel, S.; Lesimple, A.; Mamer, O. A.; Rokach, J.; Powell, W. S. (2008). "Structural
Requirements for Activation of the 5-Oxo-6E,8Z, 11Z,14Z-eicosatetraenoic Acid (5-Oxo-ETE) Receptor: Identification of a Mead Acid Metabolite with Potent Agonist Activity".
496:(AA). AA has the same chain length as Mead acid but an additional ω-6 double bond. When physiological levels of arachidonic acid are low, other unsaturated fatty acids including mead and linoleic acid are oxidized by COX. Cyclooxygenase breaks the
656:
Oliw, E.H.; Hornsten, L.; Sprecher, H.; Hamberg, M. (1993). "Oxygenation of 5,8,11-Eicosatrienoic Acid by
Prostaglandin Endoperoxide Synthase and by Cytochrome P450 Monooxygenase: Structure and Mechanism of Formation of Major Metabolites".
461:
and suspected EFA deficiency; they were found to have blood-levels of mead acid about 13-fold higher than reference subjects. Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate
457:(EFAs) in humans and other mammals. Both are 18 carbon fatty acids unlike mead acid, which has 20 carbons. Linoleic is an ω-6 fatty acid whereas linolenic is ω-3 and mead is ω-9. One study examined patients with
863:
Hamazaki, Tomohito; Suzuki, Nobuo; Widyowati, Retno; Miyahara, Tatsuro; Kadota, Shigetoshi; Ochiai, Hiroshi; Hamazaki, Kei (2008). "The
Depressive Effects of 5,8,11-Eicosatrienoic Acid (20:3n-9) on Osteoblasts".
417:
double bonds, as is typical for polyunsaturated fatty acids. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3 (n-9). (See
350:
797:
Phinney SD, Odin RS, Johnson SB, Holman RT (1990). "Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans".
270:
833:
244:
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-
254:
InChI=1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-
781:
488:
are enzymes known to play a large role in inflammatory processes through oxidation of unsaturated fatty acids, most notably, the formation of
1123:
102:
616:"Identification of genes and pathways involved in the synthesis of Mead acid (20:3n−9), an indicator of essential fatty acid deficiency"
595:
526:
235:
388:
1507:
1501:
720:
693:
959:
Wei YF, Evans RW, Morrison AR, Sprechert H, Jakschik BA (1985). "Double bond requirement for the 5-lipoxygenase pathway".
357:
585:
434:
178:
1447:
530:
199:
1572:
1643:
1560:
1441:
1435:
470:−9). This has been documented to a lesser extent in vegetarians and semi-vegetarians following an unbalanced diet.
377:
1471:
721:"Criteria for essential fatty acid deficiency in plasma as assessed by capillary column gas–liquid chromatography"
1710:
1566:
1116:
1429:
841:
1763:
1865:
1417:
1368:
1362:
1356:
1423:
1637:
1597:
1591:
1532:
1405:
529:
to 5-oxoeicosatrienoic acid (5-oxo-ETrE). 5-Oxo-ETrE is as potent as its arachidonic acid-derived analog,
1826:
1818:
1799:
1780:
1374:
1667:
1661:
1518:
1489:
1483:
1477:
1350:
1838:
1544:
1538:
1411:
615:
477:
activity. This may be important in treating conditions where inhibition of bone formation is desired.
1860:
1619:
1495:
1399:
1393:
1320:
1109:
454:
450:
385:
38:
515:
511:
216:
1465:
1453:
554:
413:
68:
1745:
1721:
1678:
1583:
1385:
1088:
897:
545:) and therefore may be, like 5-oxo-ETE, a mediator of human allergic and inflammatory reactions.
373:
497:
1832:
1609:
1284:
1260:
1224:
1080:
1072:
1036:
1018:
976:
941:
889:
881:
814:
777:
742:
674:
635:
591:
142:
1686:
1655:
1526:
1459:
1344:
1308:
1248:
1064:
1026:
1010:
968:
931:
873:
806:
732:
666:
627:
493:
489:
408:
293:
187:
78:
1296:
1278:
1272:
1212:
1188:
426:
404:
220:
122:
1704:
1649:
1631:
1326:
1254:
1200:
1152:
1031:
998:
522:
485:
430:
328:
936:
1854:
1807:
1788:
1757:
1692:
1625:
1603:
1314:
1302:
1236:
1230:
1218:
1182:
1176:
1144:
972:
565:
458:
446:
1092:
167:
1735:
1698:
1554:
1332:
1290:
1266:
1242:
1170:
1164:
1158:
901:
422:
1014:
737:
916:
750:
631:
1751:
1338:
1206:
1194:
697:
602:
One of these is 20:3ω9, termed 'Mead acid' after its discovery by James Mead....
508:
1729:
1136:
877:
560:
538:
534:
474:
463:
418:
316:
133:
1076:
1022:
885:
1068:
810:
392:
1084:
1040:
893:
670:
639:
980:
945:
818:
746:
678:
620:
Biochimica et
Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
587:
Basic neurochemistry: molecular, cellular, and medical aspects, Volume 1
501:
154:
1101:
25:
500:
C-H bond of AA to synthesize prostaglandin H2, but breaks a stronger
917:"Conversion of 5,8,11-Eicosatrienoic Acid to Leukotrienes C3 and D3"
403:
Mead acid, also referred to as eicosatrienoic acid, is chemically a
327:
Except where otherwise noted, data are given for materials in their
834:"Essential Polyunsaturated Fatty Acids and Early Human Development"
376:, first characterized by James F. Mead. As with some other omega-9
1132:
542:
113:
101:
91:
1105:
999:"The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor"
541:; it presumably does so by binding to the 5-oxo-ETE receptor (
421:
for an explanation of the naming system.) In the presence of
719:
EN Siguel; KM Chee; JX Gong; EJ Schaefer (October 1, 1987).
204:
384:. Its elevated presence in the blood is an indication of
345:
525:
to 5-hydroxyeicosatrienoic acid (5-HETrE) and then by
1057:
1817:
1798:
1779:
1720:
1677:
1582:
1517:
1384:
1143:
992:
990:
614:Ichi I; Kono N; Arita Y; Haga S (January 2014).
557:– lists of ω-3 and ω-6 fatty acids; some others.
166:
504:C-H bond when it encounters Mead acid instead.
77:
1117:
651:
649:
8:
584:Siegel, George J.; Albers, R. Wayne (2006).
391:. Mead acid is found in large quantities in
997:Powell, William S.; Rokach, Joshua (2013).
1124:
1110:
1102:
219:
141:
17:
1030:
935:
736:
437:(HETE) and hydroperoxy (HpETE) products.
186:
776:. Oxford University Press. p. 174.
533:(5-oxo-ETE), in stimulating human blood
659:Archives of Biochemistry and Biophysics
576:
275:
240:
215:
694:"PROSTAGLANDINS AND RELATED COMPOUNDS"
590:(7th ed.). Elsevier. p. 40.
473:Mead acid has been found to decrease
247:Key: UNSRRHDPHVZAHH-YOILPLPUSA-N
121:
7:
832:Hornstra, Gerard (September 2007).
257:Key: UNSRRHDPHVZAHH-YOILPLPUBD
157:
1508:6,9,12,15,18,21-Tetracosahexaenoic
278:CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O
14:
1502:9,12,15,18,21-Tetracosapentaenoic
527:5-hydroxyeicosanoid dehydrogenase
407:with a 20-carbon chain and three
335:
24:
924:Journal of Biological Chemistry
507:Mead acid is also converted to
331:(at 25 °C , 100 kPa).
419:Fatty acid § Nomenclature
1:
1015:10.1016/j.plipres.2013.09.001
937:10.1016/S0021-9258(19)69773-5
772:Geissler C, Powers H (2017).
433:, mead acid can form various
380:, animals can make Mead acid
973:10.1016/0090-6980(85)90078-4
632:10.1016/j.bbalip.2013.10.013
521:Mead acid is metabolized by
459:intestinal fat malabsorption
435:hydroxyeicosatetraenoic acid
55:)-Icosa-5,8,11-trienoic acid
738:10.1093/clinchem/33.10.1869
531:5-oxo-eicosatetraenoic acid
378:polyunsaturated fatty acids
1882:
1003:Progress in Lipid Research
466:to make mead acid, (20:3,
878:10.1007/s11745-008-3252-8
325:
286:
266:
231:
61:
37:
32:
23:
1561:7,10,13-Octadecatrienoic
1069:10.1124/jpet.107.134908
838:Fats of Life Newsletter
321:306.48276
1711:7,10,13-Eicosatrienoic
1567:9,12,15-Eicosatrienoic
915:Hammarström S (1981).
671:10.1006/abbi.1993.1425
811:10.1093/ajcn/51.3.385
753:on September 27, 2011
455:essential fatty acids
481:Role in inflammation
451:alpha-linolenic acid
386:essential fatty acid
39:Preferred IUPAC name
692:Cyberlipid Center.
555:Polyunsaturated fat
20:
1764:8,11-Eicosadienoic
1644:Dihomo-γ-linolenic
1573:β-Eicosatetraenoic
1472:Dihomo-α-linolenic
1357:Heptatriacontanoic
783:9 78-0-19-876802-9
725:Clinical Chemistry
374:omega-9 fatty acid
358:Infobox references
18:
1848:
1847:
1369:Nonatriacontanoic
1363:Octatriacontanoic
799:Am. J. Clin. Nutr
731:(10): 1869–1873.
700:on April 13, 2018
453:, are considered
445:Two fatty acids,
366:Chemical compound
364:
363:
200:CompTox Dashboard
103:Interactive image
1873:
1819:ω−12 Unsaturated
1800:ω−11 Unsaturated
1781:ω−10 Unsaturated
1484:Eicosapentaenoic
1478:Eicosatetraenoic
1442:Palmitolinolenic
1436:Myristolinolenic
1351:Hexatriacontylic
1126:
1119:
1112:
1103:
1097:
1096:
1051:
1045:
1044:
1034:
994:
985:
984:
956:
950:
949:
939:
930:(3): 2275–2279.
921:
912:
906:
905:
860:
854:
853:
851:
849:
840:. Archived from
829:
823:
822:
794:
788:
787:
769:
763:
762:
760:
758:
749:. Archived from
740:
716:
710:
709:
707:
705:
696:. Archived from
689:
683:
682:
653:
644:
643:
611:
605:
604:
581:
494:arachidonic acid
490:prostaglandin H2
348:
342:
339:
338:
294:Chemical formula
224:
223:
208:
206:
190:
170:
159:
145:
125:
105:
81:
28:
21:
1881:
1880:
1876:
1875:
1874:
1872:
1871:
1870:
1851:
1850:
1849:
1844:
1813:
1794:
1775:
1722:ω−9 Unsaturated
1716:
1679:ω−7 Unsaturated
1673:
1638:Dihomo-linoleic
1598:12-Octadecenoic
1592:8-Tetradecenoic
1584:ω−6 Unsaturated
1578:
1533:Palmitovaccenic
1519:ω−5 Unsaturated
1513:
1496:Docosahexaenoic
1430:Myristolinoleic
1424:Myristovaccenic
1386:ω−3 Unsaturated
1380:
1321:Hentriacontylic
1139:
1130:
1100:
1053:
1052:
1048:
996:
995:
988:
958:
957:
953:
919:
914:
913:
909:
862:
861:
857:
847:
845:
844:on June 7, 2008
831:
830:
826:
796:
795:
791:
784:
774:Human Nutrition
771:
770:
766:
756:
754:
718:
717:
713:
703:
701:
691:
690:
686:
655:
654:
647:
613:
612:
608:
598:
583:
582:
578:
574:
551:
486:Cyclooxygenases
483:
443:
427:cytochrome p450
405:carboxylic acid
401:
367:
360:
355:
354:
353: ?)
344:
340:
336:
332:
310:
306:
302:
296:
282:
279:
274:
273:
262:
259:
258:
255:
249:
248:
245:
239:
238:
227:
209:
202:
193:
173:
160:
148:
128:
108:
95:
84:
71:
57:
56:
12:
11:
5:
1879:
1877:
1869:
1868:
1866:Alkenoic acids
1863:
1853:
1852:
1846:
1845:
1843:
1842:
1836:
1830:
1827:4-Hexadecenoic
1823:
1821:
1815:
1814:
1812:
1811:
1804:
1802:
1796:
1795:
1793:
1792:
1785:
1783:
1777:
1776:
1774:
1773:
1767:
1761:
1755:
1749:
1743:
1733:
1726:
1724:
1718:
1717:
1715:
1714:
1708:
1702:
1696:
1690:
1683:
1681:
1675:
1674:
1672:
1671:
1665:
1659:
1653:
1647:
1641:
1635:
1629:
1623:
1617:
1607:
1601:
1595:
1588:
1586:
1580:
1579:
1577:
1576:
1570:
1564:
1558:
1552:
1542:
1536:
1530:
1523:
1521:
1515:
1514:
1512:
1511:
1505:
1499:
1493:
1487:
1481:
1475:
1469:
1463:
1457:
1451:
1445:
1439:
1433:
1427:
1421:
1415:
1409:
1403:
1397:
1390:
1388:
1382:
1381:
1379:
1378:
1375:Tetracontanoic
1372:
1366:
1360:
1354:
1348:
1342:
1336:
1330:
1324:
1318:
1312:
1306:
1300:
1294:
1288:
1282:
1276:
1270:
1264:
1258:
1252:
1246:
1240:
1234:
1228:
1222:
1216:
1210:
1204:
1198:
1192:
1186:
1180:
1174:
1168:
1162:
1156:
1149:
1147:
1141:
1140:
1131:
1129:
1128:
1121:
1114:
1106:
1099:
1098:
1063:(2): 698–707.
1046:
1009:(4): 651–665.
986:
961:Prostaglandins
951:
907:
855:
824:
789:
782:
764:
711:
684:
665:(2): 288–297.
645:
626:(1): 204–213.
606:
596:
575:
573:
570:
569:
568:
563:
558:
550:
547:
523:5-lipoxygenase
482:
479:
442:
439:
431:cyclooxygenase
400:
397:
365:
362:
361:
356:
334:
333:
329:standard state
326:
323:
322:
319:
313:
312:
308:
304:
300:
297:
292:
289:
288:
284:
283:
281:
280:
277:
269:
268:
267:
264:
263:
261:
260:
256:
253:
252:
250:
246:
243:
242:
234:
233:
232:
229:
228:
226:
225:
217:DTXSID10920487
212:
210:
198:
195:
194:
192:
191:
183:
181:
175:
174:
172:
171:
163:
161:
153:
150:
149:
147:
146:
138:
136:
130:
129:
127:
126:
118:
116:
110:
109:
107:
106:
98:
96:
89:
86:
85:
83:
82:
74:
72:
67:
64:
63:
59:
58:
42:
41:
35:
34:
30:
29:
13:
10:
9:
6:
4:
3:
2:
1878:
1867:
1864:
1862:
1859:
1858:
1856:
1840:
1837:
1834:
1831:
1828:
1825:
1824:
1822:
1820:
1816:
1809:
1806:
1805:
1803:
1801:
1797:
1790:
1787:
1786:
1784:
1782:
1778:
1771:
1768:
1765:
1762:
1759:
1756:
1753:
1750:
1747:
1744:
1741:
1737:
1734:
1731:
1728:
1727:
1725:
1723:
1719:
1712:
1709:
1706:
1703:
1700:
1697:
1694:
1691:
1688:
1685:
1684:
1682:
1680:
1676:
1669:
1666:
1663:
1660:
1657:
1654:
1651:
1648:
1645:
1642:
1639:
1636:
1633:
1630:
1627:
1624:
1621:
1618:
1615:
1611:
1608:
1605:
1602:
1599:
1596:
1593:
1590:
1589:
1587:
1585:
1581:
1574:
1571:
1568:
1565:
1562:
1559:
1556:
1553:
1550:
1546:
1545:β-Eleostearic
1543:
1540:
1539:α-Eleostearic
1537:
1534:
1531:
1528:
1525:
1524:
1522:
1520:
1516:
1509:
1506:
1503:
1500:
1497:
1494:
1491:
1488:
1485:
1482:
1479:
1476:
1473:
1470:
1467:
1464:
1461:
1458:
1455:
1452:
1449:
1446:
1443:
1440:
1437:
1434:
1431:
1428:
1425:
1422:
1419:
1418:Laurolinoleic
1416:
1413:
1410:
1407:
1404:
1401:
1398:
1395:
1392:
1391:
1389:
1387:
1383:
1376:
1373:
1370:
1367:
1364:
1361:
1358:
1355:
1352:
1349:
1346:
1343:
1340:
1337:
1334:
1331:
1328:
1325:
1322:
1319:
1316:
1313:
1310:
1307:
1304:
1301:
1298:
1295:
1292:
1289:
1286:
1283:
1280:
1277:
1274:
1271:
1268:
1265:
1262:
1259:
1256:
1253:
1250:
1247:
1244:
1241:
1238:
1235:
1232:
1229:
1226:
1223:
1220:
1217:
1214:
1211:
1208:
1205:
1202:
1199:
1196:
1193:
1190:
1187:
1184:
1181:
1178:
1175:
1172:
1169:
1166:
1163:
1160:
1157:
1154:
1151:
1150:
1148:
1146:
1142:
1138:
1134:
1127:
1122:
1120:
1115:
1113:
1108:
1107:
1104:
1094:
1090:
1086:
1082:
1078:
1074:
1070:
1066:
1062:
1058:
1050:
1047:
1042:
1038:
1033:
1028:
1024:
1020:
1016:
1012:
1008:
1004:
1000:
993:
991:
987:
982:
978:
974:
970:
967:(4): 537–45.
966:
962:
955:
952:
947:
943:
938:
933:
929:
925:
918:
911:
908:
903:
899:
895:
891:
887:
883:
879:
875:
872:(2): 97–102.
871:
867:
859:
856:
843:
839:
835:
828:
825:
820:
816:
812:
808:
805:(3): 385–92.
804:
800:
793:
790:
785:
779:
775:
768:
765:
752:
748:
744:
739:
734:
730:
726:
722:
715:
712:
699:
695:
688:
685:
680:
676:
672:
668:
664:
660:
652:
650:
646:
641:
637:
633:
629:
625:
621:
617:
610:
607:
603:
599:
597:9780080472072
593:
589:
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566:Prostaglandin
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447:linoleic acid
440:
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411:-interrupted
410:
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46:
40:
36:
31:
27:
22:
16:
1839:8-Eicosenoic
1833:Petroselinic
1769:
1739:
1613:
1610:Linolelaidic
1548:
1490:Clupanodonic
1448:Palmitidonic
1285:Pentacosylic
1261:Heneicosylic
1225:Pentadecylic
1060:
1056:
1049:
1006:
1002:
964:
960:
954:
927:
923:
910:
869:
865:
858:
846:. Retrieved
842:the original
837:
827:
802:
798:
792:
773:
767:
755:. Retrieved
751:the original
728:
724:
714:
702:. Retrieved
698:the original
687:
662:
658:
623:
619:
609:
601:
586:
579:
520:
509:leukotrienes
506:
484:
475:osteoblastic
472:
467:
444:
423:lipoxygenase
412:
402:
381:
369:
368:
62:Identifiers
52:
48:
44:
15:
1861:Fatty acids
1687:Palmitoleic
1656:Arachidonic
1620:γ-Linolenic
1527:Myristoleic
1466:α-Parinaric
1460:Stearidonic
1454:α-Linolenic
1406:Decadienoic
1345:Ceroplastic
1309:Nonacosylic
1249:Nonadecylic
1137:fatty acids
848:October 23,
757:October 24,
704:October 24,
539:neutrophils
535:eosinophils
287:Properties
123:CHEBI:72865
1855:Categories
1297:Carboceric
1279:Lignoceric
1273:Tricosylic
1213:Tridecylic
1189:Pelargonic
572:References
561:Eicosanoid
498:bisallylic
464:oleic acid
441:Physiology
389:deficiency
317:Molar mass
188:JQS194YH3X
134:ChemSpider
90:3D model (
79:20590-32-3
69:CAS Number
19:Mead acid
1705:Paullinic
1650:Sciadonic
1632:Pinolenic
1412:Lauroleic
1327:Lacceroic
1255:Arachidic
1201:Undecylic
1153:Propionic
1145:Saturated
1077:0022-3565
1023:0163-7827
886:0024-4201
409:methylene
399:Chemistry
393:cartilage
370:Mead acid
1808:Gadoleic
1789:Sapienic
1758:Nervonic
1693:Vaccenic
1626:Calendic
1604:Linoleic
1400:Decenoic
1394:Octenoic
1315:Melissic
1303:Montanic
1237:Margaric
1231:Palmitic
1219:Myristic
1183:Caprylic
1177:Enanthic
1093:19936422
1085:18292294
1041:24056189
894:18941818
640:24184513
549:See also
1746:Gondoic
1736:Elaidic
1699:Rumenic
1662:Adrenic
1555:Punicic
1333:Psyllic
1291:Cerotic
1267:Behenic
1243:Stearic
1171:Caproic
1165:Valeric
1159:Butyric
1032:5710732
981:2988021
946:6780563
902:4011759
819:2106775
747:3665042
679:8373167
502:allylic
382:de novo
351:what is
349: (
311:
168:5312531
155:PubChem
143:4471956
1841:(20:1)
1835:(18:1)
1829:(16:1)
1810:(20:1)
1791:(16:1)
1772:(20:3)
1766:(20:2)
1760:(24:1)
1754:(22:1)
1752:Erucic
1748:(20:1)
1742:-18:1)
1732:(18:1)
1713:(20:3)
1707:(20:1)
1701:(18:2)
1695:(18:1)
1689:(16:1)
1670:(22:5)
1668:Osbond
1664:(22:4)
1658:(20:4)
1652:(20:3)
1646:(20:3)
1640:(20:2)
1634:(18:3)
1628:(18:3)
1622:(18:3)
1616:-18:2)
1606:(18:2)
1600:(18:1)
1594:(14:1)
1575:(20:4)
1569:(20:3)
1563:(18:3)
1557:(18:3)
1551:-18:3)
1541:(18:3)
1535:(16:1)
1529:(14:1)
1510:(24:6)
1504:(24:5)
1498:(22:6)
1492:(22:5)
1486:(20:5)
1480:(20:4)
1474:(20:3)
1468:(18:4)
1462:(18:4)
1456:(18:3)
1450:(16:4)
1444:(16:3)
1438:(14:3)
1432:(14:2)
1426:(14:1)
1420:(12:2)
1414:(12:1)
1408:(10:2)
1402:(10:1)
1339:Geddic
1207:Lauric
1195:Capric
1133:Lipids
1091:
1083:
1075:
1039:
1029:
1021:
979:
944:
900:
892:
884:
866:Lipids
817:
780:
745:
677:
638:
594:
372:is an
346:verify
343:
271:SMILES
33:Names
1740:trans
1730:Oleic
1614:trans
1549:trans
1396:(8:1)
1377:(C40)
1371:(C39)
1365:(C38)
1359:(C37)
1353:(C36)
1347:(C35)
1341:(C34)
1335:(C33)
1329:(C32)
1323:(C31)
1317:(C30)
1311:(C29)
1305:(C28)
1299:(C27)
1293:(C26)
1287:(C25)
1281:(C24)
1275:(C23)
1269:(C22)
1263:(C21)
1257:(C20)
1251:(C19)
1245:(C18)
1239:(C17)
1233:(C16)
1227:(C15)
1221:(C14)
1215:(C13)
1209:(C12)
1203:(C11)
1197:(C10)
1089:S2CID
920:(PDF)
898:S2CID
543:OXER1
492:from
429:, or
236:InChI
114:ChEBI
92:JSmol
1770:Mead
1191:(C9)
1185:(C8)
1179:(C7)
1173:(C6)
1167:(C5)
1161:(C4)
1155:(C3)
1081:PMID
1073:ISSN
1037:PMID
1019:ISSN
977:PMID
942:PMID
890:PMID
882:ISSN
850:2007
815:PMID
778:ISBN
759:2007
743:PMID
706:2007
675:PMID
636:PMID
624:1841
592:ISBN
537:and
514:and
449:and
179:UNII
1065:doi
1061:325
1027:PMC
1011:doi
969:doi
932:doi
928:256
874:doi
807:doi
733:doi
667:doi
663:305
628:doi
414:cis
205:EPA
158:CID
51:,11
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1087:.
1079:.
1071:.
1059:.
1035:.
1025:.
1017:.
1007:52
1005:.
1001:.
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516:D3
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630::
468:n
341:N
309:2
307:O
303:H
299:C
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45:Z
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