399:
250:
623:
33:
644:
24:
705:
521:
678:
661:
135:
422:
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
432:
InChI=1/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
1128:
1466:
1417:
1412:
1342:
1121:
1626:
534:
1556:
1352:
1347:
1114:
1422:
1439:
792:
448:
788:
733:
As a molecule naturally enriched in the eye lens, lanosterol is a component involved in maintenance of lens clarity. Its proposed
1337:
286:
1180:
1185:
529:
1033:
413:
1332:
541:
1514:
1327:
571:. In the eyes of vertebrates, lanosterol is a natural constituent, having a role in maintaining health of the
55:
1278:
356:
245:
1362:
1257:
1229:
713:
377:
323:
187:
1591:
1524:
1357:
1252:
1247:
709:
572:
257:
1218:
394:
317:
1106:
1296:
1505:
1385:
1315:
1144:
649:
608:
1566:
1273:
1242:
1026:
717:
45:
756:. However, supplemental lanosterol in eye drops appears to have limited solubility and poor
207:
1666:
1576:
1471:
1449:
365:
8:
1671:
734:
666:
101:
1011:
398:
249:
167:
111:
1152:
1080:
992:
965:
934:
909:
886:
861:
147:
833:
1395:
997:
939:
837:
636:
628:
820:
Schaller, Hubert (May 2003). "The role of sterols in plant growth and development".
1661:
1213:
1019:
987:
977:
929:
921:
881:
873:
829:
677:
660:
622:
471:
345:
84:)-3a,6,6,9a,11a-Pentamethyl-1--2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1
1175:
1066:
910:"Failure of oxysterols such as lanosterol to restore lens clarity from cataracts"
757:
694:
656:
2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol
643:
1636:
1621:
1603:
1237:
1070:
1046:
925:
760:
in the eye, and has not proved effective for inhibiting cataracts, as of 2020.
512:
708:
Simplified version of the lanosterol synthesis pathway with the intermediates
1655:
1571:
1200:
690:
689:
Elaboration of lanosterol under enzyme catalysis leads to other steroids. 14-
500:
238:
748:
Lanosterol is under research for its potential as a therapeutic additive in
1561:
1551:
1085:
1001:
943:
841:
796:
784:
769:
568:
560:
32:
1587:
1492:
1481:
1476:
1454:
1444:
1377:
1137:
1095:
1075:
982:
698:
576:
557:
227:
1631:
1611:
1581:
1543:
1461:
1434:
1427:
1288:
1170:
1042:
780:
738:
490:
276:
258:
198:
877:
23:
1616:
1061:
511:
Except where otherwise noted, data are given for materials in their
1390:
1301:
1136:
908:
Daszynski DM, Santhoshkumar P, Phadte AS, et al. (June 2019).
753:
749:
742:
721:
704:
616:
306:
218:
907:
590:
The biosynthesis of lanosterol has been intensively investigated.
134:
1497:
1208:
1190:
1162:
1141:
564:
332:
1050:
752:
to inhibit the aggregation of crystallin proteins and dissolve
178:
774:
612:
158:
124:
382:
505:
138 to 140 °C (280 to 284 °F; 411 to 413 K)
297:
567:
are derived. By contrast, plant steroids are produced via
1041:
741:, which contribute to the clouding of vision by forming
728:
563:
and is the compound from which all animal and fungal
285:
1653:
344:
862:"Biosynthesis of cholesterol and other sterols"
110:
456:C(CCC=C(C)C)1CC2(C)C1CCC3=C2CC4C(C)(C)(O)CC34C
1122:
1027:
964:Xu J, Fu Q, Chen X, Yao K (November 2020).
963:
1129:
1115:
1034:
1020:
966:"Advances in pharmacotherapy of cataracts"
397:
248:
206:
991:
981:
933:
885:
364:
819:
703:
393:
322:
226:
1654:
724:shown. Some intermediates are omitted.
239:
1110:
1015:
903:
901:
899:
897:
855:
853:
851:
425:Key: CAHGCLMLTWQZNJ-BQNIITSRSA-N
186:
166:
959:
957:
955:
953:
859:
435:Key: CAHGCLMLTWQZNJ-BQNIITSRBP
335:
305:
13:
894:
848:
729:Research as an eye drop supplement
575:. Lanosterol is the precursor to
14:
1683:
950:
737:is to inhibit the aggregation of
970:Annals of Translational Medicine
676:
659:
642:
621:
519:
31:
22:
585:
515:(at 25 °C , 100 kPa).
813:
1:
834:10.1016/S0163-7827(02)00047-4
806:
1279:Geranylgeranyl pyrophosphate
7:
1258:Dimethylallyl pyrophosphate
763:
714:dimethylallyl pyrophosphate
611:condense with reduction by
88:-cyclopentaphenanthren-7-ol
10:
1688:
926:10.1038/s41598-019-44676-4
822:Progress in Lipid Research
495:426.71 g/mol
1601:
1541:
1534:
1490:
1375:
1323:
1314:
1287:
1266:
1253:Isopentenyl pyrophosphate
1248:5-Diphosphomevalonic acid
1227:
1199:
1160:
1151:
1057:
710:isopentenyl pyrophosphate
509:
464:
444:
409:
94:
54:
44:
39:
30:
21:
635:Squalene is oxidized to
1467:Cholesta-7,24-dien-3-ol
1418:4alpha-Methylzymosterol
1297:Prephytoene diphosphate
1145:metabolic intermediates
49:Lanosta-8,24-dien-3β-ol
1386:Farnesyl pyrophosphate
1316:Non-mevalonate pathway
860:Nes, W. David (2011).
725:
650:squalene monooxygenase
609:farnesyl pyrophosphate
1519:-Dihydroxycholesterol
1413:14-demethyllanosterol
1274:Geranyl pyrophosphate
1243:Phosphomevalonic acid
1219:β-Hydroxybutyric acid
718:geranyl pyrophosphate
707:
56:Systematic IUPAC name
1577:24-Methylenelophenol
1472:7-Dehydrodesmosterol
1450:7-Dehydrocholesterol
983:10.21037/atm-20-1960
1567:4α-methylfecosterol
1510:-Hydroxycholesterol
739:crystallin proteins
735:mechanism of action
667:lanosterol synthase
148:Beilstein Reference
18:
1153:Mevalonate pathway
1081:Dihydrotachysterol
914:Scientific Reports
779:Other tetracyclic
726:
697:eventually yields
639:(squalene epoxide)
542:Infobox references
16:
1649:
1648:
1645:
1644:
1396:2,3-Oxidosqualene
1371:
1370:
1310:
1309:
1104:
1103:
878:10.1021/cr200021m
872:(10): 6423–6451.
693:of lanosterol by
687:
686:
637:2,3-oxidosqualene
629:squalene synthase
607:Two molecules of
550:Chemical compound
548:
547:
378:CompTox Dashboard
136:Interactive image
1679:
1627:Ergostatetraenol
1539:
1538:
1498:Steroid hormones
1321:
1320:
1214:Acetoacetic acid
1158:
1157:
1131:
1124:
1117:
1108:
1107:
1036:
1029:
1022:
1013:
1012:
1006:
1005:
995:
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961:
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947:
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891:
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866:Chemical Reviews
857:
846:
845:
817:
680:
663:
646:
625:
593:
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532:
526:
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472:Chemical formula
402:
401:
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309:
289:
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35:
26:
19:
15:
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1651:
1650:
1641:
1597:
1530:
1495:
1486:
1367:
1306:
1283:
1262:
1223:
1195:
1176:Acetoacetyl-CoA
1147:
1135:
1105:
1100:
1071:Ergocalciferols
1067:Cholecalciferol
1053:
1047:membrane lipids
1040:
1010:
1009:
962:
951:
906:
895:
858:
849:
818:
814:
809:
803:
766:
758:bioavailability
731:
588:
582:
551:
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538:
537: ?)
528:
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150:
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90:
89:
50:
12:
11:
5:
1685:
1675:
1674:
1669:
1664:
1647:
1646:
1643:
1642:
1640:
1639:
1637:Ergocalciferol
1634:
1629:
1624:
1622:Ergostatrienol
1619:
1614:
1608:
1606:
1604:Ergocalciferol
1599:
1598:
1596:
1595:
1584:
1579:
1574:
1569:
1564:
1559:
1557:Cycloeucalenol
1554:
1548:
1546:
1536:
1532:
1531:
1529:
1528:
1521:
1512:
1502:
1500:
1488:
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1276:
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1268:
1264:
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1261:
1260:
1255:
1250:
1245:
1240:
1238:Mevalonic acid
1234:
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1225:
1224:
1222:
1221:
1216:
1211:
1205:
1203:
1197:
1196:
1194:
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1073:
1064:
1058:
1055:
1054:
1039:
1038:
1031:
1024:
1016:
1008:
1007:
949:
893:
847:
828:(3): 163–175.
811:
810:
808:
805:
801:
800:
777:
772:
765:
762:
730:
727:
685:
684:
681:
674:
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657:
653:
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632:
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626:
619:
604:
603:
600:
597:
587:
584:
549:
546:
545:
540:
518:
517:
513:standard state
510:
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390:
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353:
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1607:
1605:
1600:
1593:
1589:
1585:
1583:
1580:
1578:
1575:
1573:
1572:Isofucosterol
1570:
1568:
1565:
1563:
1560:
1558:
1555:
1553:
1550:
1549:
1547:
1545:
1540:
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1504:
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1379:
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1359:
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1231:
1226:
1220:
1217:
1215:
1212:
1210:
1207:
1206:
1204:
1202:
1201:Ketone bodies
1198:
1192:
1189:
1187:
1184:
1182:
1179:
1177:
1174:
1172:
1169:
1168:
1166:
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1159:
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1139:
1132:
1127:
1125:
1120:
1118:
1113:
1112:
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1092:
1089:
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1084:
1082:
1079:
1077:
1074:
1072:
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1063:
1060:
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1048:
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1037:
1032:
1030:
1025:
1023:
1018:
1017:
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994:
989:
984:
979:
975:
971:
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941:
936:
931:
927:
923:
919:
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911:
904:
902:
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883:
879:
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871:
867:
863:
856:
854:
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843:
839:
835:
831:
827:
823:
816:
812:
804:
798:
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790:
786:
782:
778:
776:
773:
771:
768:
767:
761:
759:
755:
751:
746:
744:
740:
736:
723:
719:
715:
711:
706:
702:
700:
696:
692:
691:Demethylation
682:
679:
675:
672:
671:
668:
665:
662:
658:
655:
654:
651:
648:
645:
641:
638:
634:
633:
630:
627:
624:
620:
618:
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606:
605:
601:
598:
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583:
580:
578:
574:
570:
566:
562:
559:
555:
543:
536:
531:
514:
508:
504:
502:
501:Melting point
499:
498:
494:
492:
489:
488:
476:
473:
469:
468:
463:
454:
453:
450:
443:
429:
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418:
415:
408:
400:
396:
395:DTXSID1040744
392:
391:
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367:
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281:
278:
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261:
256:
255:
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247:
244:
242:
240:ECHA InfoCard
237:
236:
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225:
224:
222:
220:
217:
216:
209:
205:
204:
202:
200:
197:
196:
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109:
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99:
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79:
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71:
67:
63:
57:
53:
47:
43:
38:
34:
29:
25:
20:
1588:Phytosterols
1562:Obtusifoliol
1552:Cycloartenol
1516:
1507:
1407:
1400:
1096:Phytosterols
1090:
1086:Fusidic acid
976:(22): 1552.
973:
969:
917:
913:
869:
865:
825:
821:
815:
802:
797:cucurbitacin
785:cycloartenol
770:Cycloartenol
747:
732:
688:
599:Illustration
589:
586:Biosynthesis
581:
569:cycloartenol
561:triterpenoid
553:
552:
188:ChEMBL225111
95:Identifiers
85:
81:
77:
73:
69:
65:
61:
1667:Triterpenes
1493:Cholesterol
1482:Cholesterol
1477:Desmosterol
1455:Cholesterol
1445:Lathosterol
1423:Zymosterone
1378:Cholesterol
1138:Cholesterol
1076:Cholesterol
1043:Cholestanes
920:(1): 8459.
781:triterpenes
720:(GPP), and
699:cholesterol
596:Description
577:cholesterol
558:tetracyclic
465:Properties
246:100.001.105
168:CHEBI:16521
17:Lanosterol
1672:Lanostanes
1656:Categories
1632:Ergosterol
1612:Fecosterol
1582:Sitosterol
1544:Sitosterol
1462:Zymosterol
1440:Zymostenol
1435:Zymosterol
1428:Zymosterol
1408:Lanosterol
1401:Lanosterol
1289:Carotenoid
1171:Acetyl-CoA
1091:Lanosterol
807:References
793:tirucallol
554:Lanosterol
491:Molar mass
366:1J05Z83K3M
324:Lanosterol
277:IUPHAR/BPS
199:ChemSpider
123:3D model (
102:CAS Number
46:IUPAC name
1617:Episterol
1062:Adosterol
754:cataracts
750:eye drops
743:cataracts
716:(DMAPP),
683:(step 2)
267:201-214-9
259:EC Number
1594:instead.
1535:Nonhuman
1527:instead.
1391:Squalene
1302:Phytoene
1267:Geranyl-
1002:33313297
944:31186457
842:12689617
764:See also
722:squalene
673:(step 2)
617:squalene
615:to form
565:steroids
485:O
219:DrugBank
153:2226449
1662:Sterols
1343:CDP-MEP
1209:Acetone
1191:HMG-CoA
1186:HMB-CoA
1163:HMG-CoA
1142:steroid
1051:sterols
993:7729355
935:6560215
887:3191736
712:(IPP),
602:Enzyme
535:what is
533: (
333:PubChem
228:DB03696
112:79-63-0
1515:20α,22
1353:HMB-PP
1338:CDP-ME
1000:
990:
942:
932:
884:
840:
795:, and
789:euphol
530:verify
527:
449:SMILES
346:246983
307:C01724
208:216175
179:ChEMBL
40:Names
1586:More
1491:From
1363:DMAPP
1348:MEcPP
1230:DMAPP
775:CYP51
695:CYP51
613:NADPH
556:is a
414:InChI
159:ChEBI
125:JSmol
1592:here
1590:see
1525:here
1523:See
1328:DOXP
1140:and
998:PMID
940:PMID
838:PMID
573:lens
357:UNII
318:MeSH
298:KEGG
287:2746
80:,11a
1602:To
1542:To
1496:to
1376:To
1358:IPP
1333:MEP
1228:to
1181:HMB
1161:to
988:PMC
978:doi
930:PMC
922:doi
882:PMC
874:doi
870:111
830:doi
383:EPA
336:CID
76:,9a
68:,5a
64:,3a
1658::
1506:22
1049::
1045:,
996:.
986:.
972:.
968:.
952:^
938:.
928:.
916:.
912:.
896:^
880:.
868:.
864:.
850:^
836:.
826:42
824:.
791:,
787:,
783::
745:.
701:.
579:.
483:50
479:30
72:,7
60:(1
1517:R
1508:R
1130:e
1123:t
1116:v
1069:/
1035:e
1028:t
1021:v
1004:.
980::
974:8
946:.
924::
918:9
890:.
876::
844:.
832::
799:.
525:N
481:H
477:C
385:)
381:(
127:)
86:H
82:R
78:S
74:S
70:R
66:R
62:R
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