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Androstenetriol

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Bezisterim, a derivative of the natural anti-inflammatory steroid β-AET, is an orally active NF-κB inhibitor. It has been shown to protect neurons by reducing inflammation and improving glucose utilization, thereby promoting brain health. Clinical results have demonstrated that bezisterim can improve
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Ahlem, Clarence N.; Auci, Dominick L.; Nicoletti, Ferdinando; Pieters, Raymond; Kennedy, Michael R.; Page, Theodore M.; Reading, Christopher L.; Enioutina, Elena Y.; Frincke, James M. (2011).
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Dillon, Joseph S. (2005). "Dehydroepiandrosterone, Dehydroepiandrosterone Sulfate and Related Steroids: Their Role in Inflammatory, Allergic and Immunological Disorders".
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InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-17,20-22H,3-9H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1
674: 1036: 1835: 1357: 900: 304: 1312: 1056: 1031: 716: 64: 591:"Molecular Targets for 17α-Ethynyl-5-Androstene-3β,7β,17β-Triol, an Anti-Inflammatory Agent Derived from the Human Metabolome" 1663: 1297: 1006: 667: 1608: 1026: 971: 430:"Pharmacology and immune modulating properties of 5-androstene-3β,7β,17β-triol, a DHEA metabolite in the human metabolome" 1648: 1643: 966: 162: 750: 1126: 182: 1533: 1106: 782: 1859: 1828: 1768: 1763: 1563: 1454: 1439: 1434: 1429: 1424: 956: 895: 832: 827: 735: 745: 519: 1543: 1538: 1528: 1523: 1444: 1111: 1066: 660: 1603: 1474: 1136: 1096: 905: 880: 777: 1758: 1367: 1197: 875: 857: 730: 1352: 910: 387: 1869: 1658: 1568: 1504: 1449: 1292: 1086: 1001: 890: 787: 740: 707: 429: 359: 1821: 1558: 1347: 1267: 694: 383: 1247: 1242: 1076: 1071: 852: 1854: 1733: 1618: 1593: 1277: 1272: 1141: 1101: 1081: 1061: 1051: 602: 198: 1773: 1493: 1400: 1382: 1372: 1342: 1011: 996: 961: 797: 405: 117: 1396: 1392: 1322: 1232: 1217: 1202: 1131: 465: 391: 1638: 1633: 1307: 1686: 1681: 1623: 1362: 1282: 1192: 867: 807: 638: 620: 558:"Rationale for an anti-inflammatory insulin sensitizer in a phase 3 Alzheimer's disease trial" 500: 457: 449: 394: 379: 375: 544:
cognition and biomarker levels in AD patients and is currently in phase III clinical trials .
1548: 1464: 1337: 1332: 1327: 1287: 1252: 1237: 1227: 1222: 1212: 1207: 1182: 1116: 885: 802: 792: 628: 610: 569: 534: 492: 441: 219: 202: 171: 1864: 1748: 1696: 1668: 1578: 1573: 1387: 1377: 1121: 1021: 1016: 986: 126: 520:"Approved drugs and natural products at clinical stages for treating Alzheimer's disease" 606: 1805: 1711: 1691: 1553: 1257: 981: 920: 812: 769: 760: 633: 590: 518:
Ma, Yajing; Liu, Sufang; Zhou, Qingfeng; Li, Zhonghua; Zhang, Zhijian; Yu, Bin (2024).
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Reading, Christopher L.; Frincke, James M.; White, Steven K. (24 February 2012).
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Reading, Chris L; Ahlem, Clarence N; Parameswaran, Narayanan (December 2021).
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11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
269: 260: 656: 187: 104:)-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1 51:
AET; Androst-5-ene-3β,7β,17β-triol; β-Androstenetriol; β-AET
362:(DHEA). It is believed to have similar effects as DHEA and 434:
The Journal of Steroid Biochemistry and Molecular Biology
366:. A study in rodents found that the compound was a weak 1809: 1720: 1492: 1410: 1150: 947: 938: 866: 768: 759: 693: 258: 245: 218: 213: 181: 161: 136: 116: 55: 47: 42: 896:11β-Hydroxyprogesterone (21-deoxycorticosterone) 150: 125: 1198:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 485:Current Drug Targets. Inflammation and Allergy 1829: 668: 8: 26: 408:) have been developed and are under study. 1836: 1822: 1193:17α-Epiestriol (16α-hydroxy-17α-estradiol) 944: 765: 675: 661: 653: 201: 34: 632: 614: 573: 170: 423: 421: 417: 309: 289: 197: 69: 977:Adrenosterone (11-ketoandrostenedione) 25: 1188:16β-Epiestriol (16β-hydroxyestradiol) 7: 1790: 1788: 527:Chinese Journal of Natural Medicines 108:-cyclopentaphenanthrene-3,7,17-triol 1358:Estradiol 3-glucuronide 17β-sulfate 141: 14: 901:18-Hydroxy-11-deoxycorticosterone 751:11β,17α,21-Trihydroxypregnenolone 1792: 230: 1107:Dihydrotestosterone glucuronide 317:Key:OEVZKEVBDIDVOI-YSZCXEEOSA-N 292:C12CC3(1CC2O)(C=C43(CC(C4)O)C)O 778:3α,5α-Tetrahydrocorticosterone 236: 224: 1: 1057:3α-Androstanediol glucuronide 539:10.1016/S1875-5364(24)60606-0 336:androst-5-ene-3β,7β,17β-triol 1808:. You can help Knowledge by 746:17α,21-Dihydroxypregnenolone 616:10.1371/journal.pone.0032147 1127:Etiocholanolone glucuronide 1112:Dihydrotestosterone sulfate 446:10.1016/j.jsbmb.2011.04.010 397:of androstenetriol such as 1886: 1787: 1027:16α-Hydroxyandrostenedione 972:11β-Hydroxyandrostenedione 957:11-Ketodihydrotestosterone 562:Alzheimer's & Dementia 374:, but did not bind to the 214:Chemical and physical data 18: 1649:7β-Hydroxyepiandrosterone 1644:7α-Hydroxyepiandrosterone 967:7β-Hydroxyepiandrosterone 401:(HE3286, NE3107; the 17α- 300: 280: 60: 33: 1534:5α-Dihydrocorticosterone 1475:Pregnanediol glucuronide 1137:Testosterone glucuronide 1097:Androsterone glucuronide 1037:16α-Hydroxy-DHEA sulfate 906:18-Hydroxycorticosterone 858:3α,5α-Tetrahydrocortisol 783:5α-Dihydrocorticosterone 497:10.2174/1568010054022079 388:glucocorticoid receptors 19:Not to be confused with 1769:11β-Hydroxyprogesterone 1764:11α-Hydroxyprogesterone 1440:20β-Dihydroprogesterone 1435:20α-Dihydroprogesterone 1430:17α-Hydroxyprogesterone 1425:16α-Hydroxyprogesterone 1353:Estradiol 3-glucuronide 833:17α-Hydroxyprogesterone 828:17α-Hydroxypregnenolone 736:17α-Hydroxypregnenolone 731:11β-Hydroxypregnenolone 1569:11-Deoxycorticosterone 1544:5β-Dihydroprogesterone 1539:5α-Dihydroprogesterone 1529:3β-Dihydroprogesterone 1524:3α-Dihydroprogesterone 1450:11-Deoxycorticosterone 1445:5α-Dihydroprogesterone 1087:Androstenediol sulfate 1067:5β-Dihydrotestosterone 911:18-Hydroxyprogesterone 891:11-Deoxycorticosterone 788:11-Deoxycorticosterone 741:21-Hydroxypregnenolone 360:dehydroepiandrosterone 1800:This article about a 1759:7α-Hydroxycholesterol 1739:Calcidiol/Calcifediol 1368:Estradiol 17β-sulfate 1348:Estradiol glucuronide 1268:27-Hydroxycholesterol 876:5α-Dihydroaldosterone 721:-Dihydroxycholesterol 1734:7-Dehydrocholesterol 1594:Pregnenolone sulfate 1142:Testosterone sulfate 1102:Androsterone sulfate 1774:Cholesterol sulfate 1509:-Hydroxycholesterol 1401:estradiol palmitate 1383:Estriol glucuronide 1373:Estrone glucuronide 1343:Estradiol disulfate 1012:Dihydrotestosterone 997:Dehydroandrosterone 962:11-Ketotestosterone 798:11-Ketoprogesterone 712:-Hydroxycholesterol 607:2012PLoSO...732147R 30: 1397:estradiol stearate 1393:Lipoidal estradiol 1323:2-Methoxyestradiol 1248:16β-Hydroxyestrone 1243:16α-Hydroxyestrone 1233:4-Methoxyestradiol 1218:4-Hydroxyestradiol 1203:2-Hydroxyestradiol 1132:Epietiocholanolone 1077:3β-Etiocholanediol 1072:3α-Etiocholanediol 868:Mineralocorticoids 853:5α-Dihydrocortisol 575:10.1002/alz.057438 1860:Human metabolites 1817: 1816: 1782: 1781: 1619:3α-Androstanediol 1488: 1487: 1363:Estradiol sulfate 1283:4-Androstenedione 1278:3β-Androstanediol 1273:3α-Androstanediol 1062:3β-Androstanediol 1052:3α-Androstanediol 934: 933: 808:21-Deoxycortisone 340:β-androstenetriol 325: 324: 271:Interactive image 183:CompTox Dashboard 16:Chemical compound 1877: 1838: 1831: 1824: 1796: 1789: 1549:Allopregnanolone 1465:Allopregnanediol 1338:4-Methoxyestriol 1333:2-Methoxyestriol 1328:2-Methoxyestrone 1313:16α-Hydroxy-DHEA 1288:5-Androstenediol 1253:16-Ketoestradiol 1238:4-Methoxyestrone 1228:4-Hydroxyestrone 1223:4-Hydroxyestriol 1213:2-Hydroxyestrone 1208:2-Hydroxyestriol 1117:Etiocholanedione 1082:Androstanetriols 1032:16α-Hydroxy-DHEA 945: 886:11-Deoxycortisol 803:21-Deoxycortisol 793:11-Deoxycortisol 766: 677: 670: 663: 654: 647: 646: 636: 618: 586: 580: 579: 577: 553: 547: 546: 524: 515: 509: 508: 480: 474: 473: 425: 350:produced in the 273: 253: 238: 232: 226: 206: 205: 191: 189: 174: 154: 144: 143: 129: 38: 31: 29: 1885: 1884: 1880: 1879: 1878: 1876: 1875: 1874: 1845: 1844: 1843: 1842: 1785: 1783: 1778: 1749:Cholecalciferol 1716: 1697:Androstadienone 1669:Etiocholanolone 1639:7β-Hydroxy-DHEA 1634:7α-Hydroxy-DHEA 1579:Isopregnanolone 1574:Epipregnanolone 1484: 1406: 1388:Estriol sulfate 1378:Estrone sulfate 1308:7α-Hydroxy-DHEA 1146: 1122:Etiocholanolone 1092:Androstenetriol 1022:Epitestosterone 1017:Epiandrosterone 987:Androstenedione 930: 862: 770:Glucocorticoids 761:Corticosteroids 755: 689: 681: 651: 650: 588: 587: 583: 555: 554: 550: 522: 517: 516: 512: 482: 481: 477: 427: 426: 419: 414: 328:Androstenetriol 321: 318: 313: 308: 307: 296: 293: 288: 287: 276: 251: 241: 235: 229: 209: 199:DTXSID201043225 185: 177: 157: 140: 132: 112: 109: 68: 67: 28:Androstenetriol 24: 17: 12: 11: 5: 1883: 1881: 1873: 1872: 1867: 1862: 1857: 1847: 1846: 1841: 1840: 1833: 1826: 1818: 1815: 1814: 1797: 1780: 1779: 1777: 1776: 1771: 1766: 1761: 1752: 1751: 1746: 1741: 1736: 1724: 1722: 1718: 1717: 1715: 1714: 1712:Estratetraenol 1709: 1704: 1699: 1694: 1692:Androstadienol 1689: 1687:3β-Androstenol 1684: 1682:3α-Androstenol 1672: 1671: 1666: 1661: 1656: 1651: 1646: 1641: 1636: 1631: 1626: 1624:3α-Androstenol 1621: 1612: 1611: 1606: 1601: 1596: 1591: 1586: 1581: 1576: 1571: 1566: 1561: 1556: 1554:Corticosterone 1551: 1546: 1541: 1536: 1531: 1526: 1517: 1516: 1511: 1498: 1496: 1490: 1489: 1486: 1485: 1483: 1482: 1477: 1472: 1467: 1458: 1457: 1452: 1447: 1442: 1437: 1432: 1427: 1422: 1416: 1414: 1408: 1407: 1405: 1404: 1390: 1385: 1380: 1375: 1370: 1365: 1360: 1355: 1350: 1345: 1340: 1335: 1330: 1325: 1316: 1315: 1310: 1305: 1300: 1295: 1290: 1285: 1280: 1275: 1270: 1261: 1260: 1258:16-Ketoestrone 1255: 1250: 1245: 1240: 1235: 1230: 1225: 1220: 1215: 1210: 1205: 1200: 1195: 1190: 1185: 1180: 1175: 1170: 1165: 1156: 1154: 1148: 1147: 1145: 1144: 1139: 1134: 1129: 1124: 1119: 1114: 1109: 1104: 1099: 1094: 1089: 1084: 1079: 1074: 1069: 1064: 1059: 1054: 1045: 1044: 1039: 1034: 1029: 1024: 1019: 1014: 1009: 1004: 999: 994: 989: 984: 982:Androstenediol 979: 974: 969: 964: 959: 953: 951: 942: 936: 935: 932: 931: 929: 928: 923: 921:Corticosterone 918: 913: 908: 903: 898: 893: 888: 883: 878: 872: 870: 864: 863: 861: 860: 855: 846: 845: 840: 835: 830: 825: 820: 815: 813:Corticosterone 810: 805: 800: 795: 790: 785: 780: 774: 772: 763: 757: 756: 754: 753: 748: 743: 738: 733: 728: 723: 714: 705: 699: 697: 691: 690: 682: 680: 679: 672: 665: 657: 649: 648: 581: 548: 533:(8): 699–710. 510: 491:(3): 377–385. 475: 416: 415: 413: 410: 364:androstenediol 352:adrenal glands 323: 322: 320: 319: 316: 314: 311: 303: 302: 301: 298: 297: 295: 294: 291: 283: 282: 281: 278: 277: 275: 274: 266: 264: 256: 255: 249: 243: 242: 239: 233: 227: 222: 216: 215: 211: 210: 208: 207: 194: 192: 179: 178: 176: 175: 167: 165: 159: 158: 156: 155: 147: 145: 134: 133: 131: 130: 122: 120: 114: 113: 111: 110: 71: 63: 62: 61: 58: 57: 53: 52: 49: 45: 44: 40: 39: 21:Androstenediol 15: 13: 10: 9: 6: 4: 3: 2: 1882: 1871: 1870:Steroid stubs 1868: 1866: 1863: 1861: 1858: 1856: 1853: 1852: 1850: 1839: 1834: 1832: 1827: 1825: 1820: 1819: 1813: 1811: 1807: 1803: 1798: 1795: 1791: 1786: 1775: 1772: 1770: 1767: 1765: 1762: 1760: 1757: 1754: 1753: 1750: 1747: 1745: 1742: 1740: 1737: 1735: 1732: 1730: 1726: 1725: 1723: 1719: 1713: 1710: 1708: 1705: 1703: 1700: 1698: 1695: 1693: 1690: 1688: 1685: 1683: 1680: 1678: 1674: 1673: 1670: 1667: 1665: 1662: 1660: 1657: 1655: 1652: 1650: 1647: 1645: 1642: 1640: 1637: 1635: 1632: 1630: 1627: 1625: 1622: 1620: 1617: 1614: 1613: 1610: 1607: 1605: 1602: 1600: 1597: 1595: 1592: 1590: 1587: 1585: 1582: 1580: 1577: 1575: 1572: 1570: 1567: 1565: 1562: 1560: 1557: 1555: 1552: 1550: 1547: 1545: 1542: 1540: 1537: 1535: 1532: 1530: 1527: 1525: 1522: 1519: 1518: 1515: 1512: 1510: 1508: 1503: 1500: 1499: 1497: 1495: 1494:Neurosteroids 1491: 1481: 1480:Pregnanetriol 1478: 1476: 1473: 1471: 1468: 1466: 1463: 1460: 1459: 1456: 1453: 1451: 1448: 1446: 1443: 1441: 1438: 1436: 1433: 1431: 1428: 1426: 1423: 1421: 1418: 1417: 1415: 1413: 1409: 1402: 1398: 1394: 1391: 1389: 1386: 1384: 1381: 1379: 1376: 1374: 1371: 1369: 1366: 1364: 1361: 1359: 1356: 1354: 1351: 1349: 1346: 1344: 1341: 1339: 1336: 1334: 1331: 1329: 1326: 1324: 1321: 1318: 1317: 1314: 1311: 1309: 1306: 1304: 1301: 1299: 1296: 1294: 1291: 1289: 1286: 1284: 1281: 1279: 1276: 1274: 1271: 1269: 1266: 1263: 1262: 1259: 1256: 1254: 1251: 1249: 1246: 1244: 1241: 1239: 1236: 1234: 1231: 1229: 1226: 1224: 1221: 1219: 1216: 1214: 1211: 1209: 1206: 1204: 1201: 1199: 1196: 1194: 1191: 1189: 1186: 1184: 1183:17α-Estradiol 1181: 1179: 1176: 1174: 1171: 1169: 1166: 1164: 1161: 1158: 1157: 1155: 1153: 1149: 1143: 1140: 1138: 1135: 1133: 1130: 1128: 1125: 1123: 1120: 1118: 1115: 1113: 1110: 1108: 1105: 1103: 1100: 1098: 1095: 1093: 1090: 1088: 1085: 1083: 1080: 1078: 1075: 1073: 1070: 1068: 1065: 1063: 1060: 1058: 1055: 1053: 1050: 1047: 1046: 1043: 1040: 1038: 1035: 1033: 1030: 1028: 1025: 1023: 1020: 1018: 1015: 1013: 1010: 1008: 1005: 1003: 1000: 998: 995: 993: 990: 988: 985: 983: 980: 978: 975: 973: 970: 968: 965: 963: 960: 958: 955: 954: 952: 950: 946: 943: 941: 937: 927: 924: 922: 919: 917: 914: 912: 909: 907: 904: 902: 899: 897: 894: 892: 889: 887: 884: 882: 879: 877: 874: 873: 871: 869: 865: 859: 856: 854: 851: 848: 847: 844: 841: 839: 836: 834: 831: 829: 826: 824: 821: 819: 816: 814: 811: 809: 806: 804: 801: 799: 796: 794: 791: 789: 786: 784: 781: 779: 776: 775: 773: 771: 767: 764: 762: 758: 752: 749: 747: 744: 742: 739: 737: 734: 732: 729: 727: 724: 722: 720: 715: 713: 711: 706: 704: 701: 700: 698: 696: 692: 688: 685: 678: 673: 671: 666: 664: 659: 658: 655: 644: 640: 635: 630: 626: 622: 617: 612: 608: 604: 601:(2): e32147. 600: 596: 592: 585: 582: 576: 571: 567: 563: 559: 552: 549: 545: 540: 536: 532: 528: 521: 514: 511: 506: 502: 498: 494: 490: 486: 479: 476: 471: 467: 463: 459: 455: 451: 447: 443: 439: 435: 431: 424: 422: 418: 411: 409: 407: 404: 400: 396: 393: 389: 385: 381: 377: 373: 369: 365: 361: 357: 353: 349: 345: 341: 337: 333: 329: 315: 310: 306: 299: 290: 286: 279: 272: 268: 267: 265: 262: 257: 250: 248: 244: 223: 221: 217: 212: 204: 200: 196: 195: 193: 184: 180: 173: 169: 168: 166: 164: 160: 153: 149: 148: 146: 139: 135: 128: 124: 123: 121: 119: 115: 107: 103: 99: 95: 91: 87: 83: 79: 75: 70: 66: 59: 54: 50: 46: 43:Clinical data 41: 37: 32: 22: 1810:expanding it 1799: 1784: 1755: 1727: 1707:Androsterone 1702:Androstenone 1675: 1664:DHEA sulfate 1654:Androsterone 1616:Androstanes: 1615: 1599:Progesterone 1589:Pregnenolone 1584:Pregnanolone 1520: 1506: 1502:Cholestanes: 1501: 1470:Pregnanediol 1462:Metabolites: 1461: 1420:Progesterone 1412:Progestogens 1320:Metabolites: 1319: 1298:DHEA sulfate 1264: 1159: 1091: 1049:Metabolites: 1048: 1042:Testosterone 1007:DHEA sulfate 992:Androsterone 940:Sex steroids 850:Metabolites: 849: 843:Progesterone 838:Pregnenolone 726:Pregnenolone 718: 709: 598: 594: 584: 565: 561: 551: 542: 530: 526: 513: 488: 484: 478: 440:(3): 87–94. 437: 433: 384:progesterone 343: 339: 335: 331: 327: 326: 105: 101: 97: 93: 89: 85: 81: 77: 73: 1855:Androstanes 1629:7-Keto-DHEA 1514:Cholesterol 1303:7-Keto-DHEA 916:Aldosterone 703:Cholesterol 403:ethynylated 254: g·mol 56:Identifiers 48:Other names 1849:Categories 1744:Calcitriol 1677:Pheromones 1521:Pregnanes: 695:Precursors 684:Endogenous 412:References 406:derivative 399:bezisterim 356:metabolite 259:3D model ( 247:Molar mass 172:Q0CZ537GC8 118:CAS Number 65:IUPAC name 1729:Vitamin D 1168:Estradiol 1160:Estranes: 1152:Estrogens 949:Androgens 823:Cortisone 625:1932-6203 454:0960-0760 395:analogues 392:Synthetic 127:2697-85-0 1455:5α-DHDOC 1163:Estetrol 926:Cortisol 818:Cortisol 687:steroids 643:22384159 595:PLOS ONE 505:16101547 462:21570467 380:estrogen 376:androgen 372:estrogen 368:androgen 1802:steroid 1756:Others: 1395:(e.g., 1265:Others: 1178:Estriol 1173:Estrone 634:3286445 603:Bibcode 470:5123272 348:steroid 346:) is a 252:306.446 220:Formula 152:9818024 138:PubChem 1865:Triols 1721:Others 717:20α,22 641:  631:  623:  568:(S9). 503:  468:  460:  452:  285:SMILES 1804:is a 1609:THDOC 1564:DHDOC 523:(PDF) 466:S2CID 386:, or 354:as a 344:β-AET 342:, or 305:InChI 261:JSmol 1806:stub 1659:DHEA 1293:DHEA 1002:DHEA 639:PMID 621:ISSN 501:PMID 458:PMID 450:ISSN 370:and 163:UNII 1604:THB 1559:DHC 629:PMC 611:doi 570:doi 535:doi 493:doi 442:doi 438:126 358:of 332:AET 188:EPA 142:CID 100:,17 96:,14 92:,13 88:,10 1851:: 1505:24 1399:, 708:22 637:. 627:. 619:. 609:. 597:. 593:. 566:17 564:. 560:. 541:. 531:22 529:. 525:. 499:. 487:. 464:. 456:. 448:. 436:. 432:. 420:^ 390:. 382:, 378:, 338:, 334:, 234:30 228:19 84:,9 80:,8 76:,7 72:(3 1837:e 1830:t 1823:v 1812:. 1731:: 1679:: 1507:S 1403:) 719:R 710:R 676:e 669:t 662:v 645:. 613:: 605:: 599:7 578:. 572:: 537:: 507:. 495:: 489:4 472:. 444:: 330:( 263:) 240:3 237:O 231:H 225:C 190:) 186:( 106:H 102:S 98:S 94:S 90:R 86:S 82:R 78:R 74:S 23:.

Index

Androstenediol

IUPAC name
CAS Number
2697-85-0
PubChem
9818024
UNII
Q0CZ537GC8
CompTox Dashboard
DTXSID201043225
Edit this at Wikidata
Formula
Molar mass
JSmol
Interactive image
SMILES
InChI
steroid
adrenal glands
metabolite
dehydroepiandrosterone
androstenediol
androgen
estrogen
androgen
estrogen
progesterone
glucocorticoid receptors
Synthetic

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