26:
423:, provide a non-invasive method for diagnosing and classifying different subtypes of PA, potentially reducing the need for more invasive procedures like adrenal vein sampling. In aldosterone-producing adrenocortical adenoma (APA), which is the main cause of primary aldosteronism, the enzyme
439:
can lead to an overexpression of CYP11B2 and increased production of aldosterone. CYP11B2 catalyzes the conversion of cortisol to 18-hydroxycortisol and then further converts it into 18-oxocortisol, making 18-oxocortisol a significant biomarker for diagnosing primary aldosteronism.
418:
The measurement of 18-oxocortisol using liquid chromatography tandem mass spectrometry has demonstrated its usefulness in distinguishing between unilateral and bilateral forms of primary aldosteronism. These measurements, along with measurements of
116:
233:
InChI=1S/C21H28O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,11,14-16,18,22,25,27H,2-7,9-10H2,1H3/t14-,15-,16-,18+,19-,20+,21-/m0/s1
476:
18-oxocortisol by attaching the oxo (=O) functional group to carbon 18 of the steroid nucleus of cortisol. This additional gene also plays a role in the biosynthesis of
249:
808:
1170:
396:, where the adrenal glands are enlarged up to six times their normal size. Increased synthesis is also found in patients with aldosterone-producing
1486:
1034:
224:
70:)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopentaphenanthrene-13-carbaldehyde
1441:
1190:
1165:
850:
1792:
1426:
1140:
801:
543:"18-hydroxycorticosterone, 18-hydroxycortisol, and 18-oxocortisol in the diagnosis of primary aldosteronism and its subtypes"
388:
of 18-oxocortisol is low. The highest synthesis of 18-oxocortisol was found in certain cases of hypertension like in type 1
1737:
1160:
1105:
453:
338:
1777:
1772:
1100:
751:"Expression of CYP11B2 in Aldosterone-Producing Adrenocortical Adenoma: Regulatory Mechanisms and Clinical Significance"
884:
1933:
1255:
469:
393:
389:
193:
1662:
1235:
916:
616:"Diagnosis of endocrine disease: 18-Oxocortisol and 18-hydroxycortisol: is there clinical utility of these steroids?"
1897:
1892:
1692:
1583:
1568:
1563:
1558:
1553:
1090:
1029:
966:
961:
869:
700:"Primary aldosteronism diagnostics: KCNJ5 mutations and hybrid steroid synthesis in aldosterone-producing adenomas"
513:
879:
1672:
1667:
1657:
1652:
1573:
1240:
1200:
794:
1732:
1603:
1265:
1225:
1039:
1014:
911:
503:
1887:
1496:
1326:
1009:
991:
864:
1481:
1044:
1787:
1697:
1633:
1578:
1421:
1220:
1135:
1024:
921:
874:
841:
1687:
1476:
1396:
828:
401:
38:
1376:
1371:
1210:
1205:
986:
518:
1862:
1747:
1722:
1406:
1401:
1270:
1230:
1215:
1195:
1185:
508:
424:
210:
1902:
1622:
1529:
1511:
1501:
1471:
1145:
1130:
1095:
931:
82:
541:
Mulatero P, di Cella SM, Monticone S, Schiavone D, Manzo M, Mengozzi G, et al. (March 2012).
1923:
1525:
1521:
1451:
1361:
1346:
1331:
1260:
498:
481:
449:
420:
323:
1767:
1762:
1436:
1928:
1815:
1810:
1752:
1491:
1411:
1321:
1001:
941:
772:
731:
680:
663:
Asbach E, Williams TA, Reincke M (June 2016). "Recent
Developments in Primary Aldosteronism".
645:
591:
564:
381:
156:
1677:
1593:
1466:
1461:
1456:
1416:
1381:
1366:
1356:
1351:
1341:
1336:
1311:
1245:
1019:
936:
926:
762:
721:
711:
672:
635:
627:
554:
465:
272:
1877:
1825:
1797:
1707:
1702:
1516:
1506:
1250:
1155:
1150:
1120:
92:
136:
1840:
1820:
1682:
1386:
1115:
1054:
946:
903:
894:
726:
699:
640:
615:
377:
332:
582:
Chiba H (July 2010). "18-hydroxycortisol, 18-oxocortisol, and 6beta-hydroxycortisol".
1917:
1608:
1110:
412:
1835:
1830:
1782:
1727:
1717:
1712:
1598:
1548:
1175:
1125:
976:
971:
859:
473:
385:
181:
1867:
1757:
1642:
1540:
1431:
1073:
1049:
836:
477:
428:
1872:
1316:
817:
354:
300:
147:
464:
genes. This crossover results in the expression of an additional gene in the
1857:
1805:
1296:
956:
408:
25:
776:
735:
716:
684:
649:
595:
568:
676:
1291:
1280:
1082:
1059:
951:
767:
750:
559:
542:
493:
373:
361:
631:
1306:
1301:
820:
461:
457:
436:
397:
357:
168:
786:
749:
Nakamura Y, Yamazaki Y, Tezuka Y, Satoh F, Sasano H (November 2016).
331:
Except where otherwise noted, data are given for materials in their
1015:
11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
614:
Lenders J, Williams T, Reincke M, Gomez-Sanchez C (January 2018).
432:
405:
127:
115:
105:
790:
372:
18-Oxocortisol has been proposed as a biomarker for certain
198:
376:. In humans, 18-oxocortisol has no biological activity on
392:(glucocorticoid-curable hyperaldosteronism) and type 3
547:
The
Journal of Clinical Endocrinology and Metabolism
1849:
1621:
1539:
1279:
1081:
1072:
1000:
902:
893:
827:
584:
Nihon Rinsho. Japanese
Journal of Clinical Medicine
1030:11β-Hydroxyprogesterone (21-deoxycorticosterone)
180:
91:
1327:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
609:
607:
605:
536:
534:
802:
698:Rege J, Turcu AF, Rainey WE (February 2020).
8:
431:production. Somatic mutations in genes like
1322:17α-Epiestriol (16α-hydroxy-17α-estradiol)
1078:
899:
809:
795:
787:
257:C12CCC(=O)C=C1CC32(C4(3CC4(C(=O)CO)O)C=O)O
155:
17:
766:
725:
715:
639:
558:
530:
254:
229:
209:
1111:Adrenosterone (11-ketoandrostenedione)
472:. The additional gene plays a role in
1317:16β-Epiestriol (16β-hydroxyestradiol)
236:Key: XUQWWIFROYJHCU-UKSDXMLSSA-N
135:
7:
384:receptors. In healthy subjects, the
1487:Estradiol 3-glucuronide 17β-sulfate
171:
427:(CYP11B2) plays a crucial role in
14:
1035:18-Hydroxy-11-deoxycorticosterone
885:11β,17α,21-Trihydroxypregnenolone
620:European Journal of Endocrinology
456:between specific regions of the
284:
24:
1236:Dihydrotestosterone glucuronide
335:(at 25 °C , 100 kPa).
912:3α,5α-Tetrahydrocorticosterone
290:
278:
1:
1191:3α-Androstanediol glucuronide
880:17α,21-Dihydroxypregnenolone
665:Exp Clin Endocrinol Diabetes
1256:Etiocholanolone glucuronide
1241:Dihydrotestosterone sulfate
394:familial hyperaldosteronism
390:familial hyperaldosteronism
1950:
1161:16α-Hydroxyandrostenedione
1106:11β-Hydroxyandrostenedione
1091:11-Ketodihydrotestosterone
448:In patients with familial
1778:7β-Hydroxyepiandrosterone
1773:7α-Hydroxyepiandrosterone
1101:7β-Hydroxyepiandrosterone
329:
312:
265:
245:
220:
75:
37:
32:
23:
1663:5α-Dihydrocorticosterone
1604:Pregnanediol glucuronide
1266:Testosterone glucuronide
1226:Androsterone glucuronide
1171:16α-Hydroxy-DHEA sulfate
1040:18-Hydroxycorticosterone
992:3α,5α-Tetrahydrocortisol
917:5α-Dihydrocorticosterone
504:18-Hydroxycorticosterone
468:, which is regulated by
415:inhibits the excretion.
1898:11β-Hydroxyprogesterone
1893:11α-Hydroxyprogesterone
1569:20β-Dihydroprogesterone
1564:20α-Dihydroprogesterone
1559:17α-Hydroxyprogesterone
1554:16α-Hydroxyprogesterone
1482:Estradiol 3-glucuronide
967:17α-Hydroxyprogesterone
962:17α-Hydroxypregnenolone
870:17α-Hydroxypregnenolone
865:11β-Hydroxypregnenolone
514:Steroid 11β-hydroxylase
411:of 18-oxocortisol, and
1698:11-Deoxycorticosterone
1673:5β-Dihydroprogesterone
1668:5α-Dihydroprogesterone
1658:3β-Dihydroprogesterone
1653:3α-Dihydroprogesterone
1579:11-Deoxycorticosterone
1574:5α-Dihydroprogesterone
1221:Androstenediol sulfate
1201:5β-Dihydrotestosterone
1045:18-Hydroxyprogesterone
1025:11-Deoxycorticosterone
922:11-Deoxycorticosterone
875:21-Hydroxypregnenolone
717:10.21037/gs.2019.10.22
1888:7α-Hydroxycholesterol
1868:Calcidiol/Calcifediol
1497:Estradiol 17β-sulfate
1477:Estradiol glucuronide
1397:27-Hydroxycholesterol
1010:5α-Dihydroaldosterone
855:-Dihydroxycholesterol
677:10.1055/s-0042-105278
402:ACTH stimulation test
368:Clinical significance
1863:7-Dehydrocholesterol
1723:Pregnenolone sulfate
1271:Testosterone sulfate
1231:Androsterone sulfate
768:10.1620/tjem.240.183
560:10.1210/jc.2011-2384
509:Aldosterone synthase
425:aldosterone synthase
1903:Cholesterol sulfate
1638:-Hydroxycholesterol
1530:estradiol palmitate
1512:Estriol glucuronide
1502:Estrone glucuronide
1472:Estradiol disulfate
1146:Dihydrotestosterone
1131:Dehydroandrosterone
1096:11-Ketotestosterone
932:11-Ketoprogesterone
846:-Hydroxycholesterol
632:10.1530/EJE-17-0563
590:(Suppl 7): 339–43.
452:type 1, there is a
308: g·mol
20:
1934:Mineralocorticoids
1526:estradiol stearate
1522:Lipoidal estradiol
1452:2-Methoxyestradiol
1377:16β-Hydroxyestrone
1372:16α-Hydroxyestrone
1362:4-Methoxyestradiol
1347:4-Hydroxyestradiol
1332:2-Hydroxyestradiol
1261:Epietiocholanolone
1211:3β-Etiocholanediol
1206:3α-Etiocholanediol
1002:Mineralocorticoids
987:5α-Dihydrocortisol
519:6β-Hydroxycortisol
499:18-Hydroxycortisol
482:18-hydroxycortisol
450:hyperaldosteronism
421:18-hydroxycortisol
360:, a metabolite of
339:Infobox references
324:18-Hydroxycortisol
313:Related compounds
18:
1911:
1910:
1748:3α-Androstanediol
1617:
1616:
1492:Estradiol sulfate
1412:4-Androstenedione
1407:3β-Androstanediol
1402:3α-Androstanediol
1196:3β-Androstanediol
1186:3α-Androstanediol
1068:
1067:
942:21-Deoxycortisone
454:genetic crossover
382:mineralocorticoid
347:Chemical compound
345:
344:
319:Related compounds
194:CompTox Dashboard
117:Interactive image
1941:
1678:Allopregnanolone
1594:Allopregnanediol
1467:4-Methoxyestriol
1462:2-Methoxyestriol
1457:2-Methoxyestrone
1442:16α-Hydroxy-DHEA
1417:5-Androstenediol
1382:16-Ketoestradiol
1367:4-Methoxyestrone
1357:4-Hydroxyestrone
1352:4-Hydroxyestriol
1342:2-Hydroxyestrone
1337:2-Hydroxyestriol
1246:Etiocholanedione
1216:Androstanetriols
1166:16α-Hydroxy-DHEA
1079:
1020:11-Deoxycortisol
937:21-Deoxycortisol
927:11-Deoxycortisol
900:
811:
804:
797:
788:
781:
780:
770:
755:Tohoku J Exp Med
746:
740:
739:
729:
719:
695:
689:
688:
660:
654:
653:
643:
611:
600:
599:
579:
573:
572:
562:
538:
466:zona fasciculata
307:
292:
286:
280:
273:Chemical formula
213:
202:
200:
184:
173:
159:
139:
119:
95:
28:
21:
1949:
1948:
1944:
1943:
1942:
1940:
1939:
1938:
1914:
1913:
1912:
1907:
1878:Cholecalciferol
1845:
1826:Androstadienone
1798:Etiocholanolone
1768:7β-Hydroxy-DHEA
1763:7α-Hydroxy-DHEA
1708:Isopregnanolone
1703:Epipregnanolone
1613:
1535:
1517:Estriol sulfate
1507:Estrone sulfate
1437:7α-Hydroxy-DHEA
1275:
1251:Etiocholanolone
1156:Epitestosterone
1151:Epiandrosterone
1121:Androstenedione
1064:
996:
904:Glucocorticoids
895:Corticosteroids
889:
823:
815:
785:
784:
748:
747:
743:
697:
696:
692:
662:
661:
657:
613:
612:
603:
586:(in Japanese).
581:
580:
576:
540:
539:
532:
527:
490:
446:
370:
348:
341:
336:
320:
305:
295:
289:
283:
275:
261:
258:
253:
252:
241:
238:
237:
234:
228:
227:
216:
211:DTXSID001317244
203:
196:
187:
174:
162:
142:
122:
109:
98:
85:
71:
19:18-Oxocortisol
12:
11:
5:
1947:
1945:
1937:
1936:
1931:
1926:
1916:
1915:
1909:
1908:
1906:
1905:
1900:
1895:
1890:
1881:
1880:
1875:
1870:
1865:
1853:
1851:
1847:
1846:
1844:
1843:
1841:Estratetraenol
1838:
1833:
1828:
1823:
1821:Androstadienol
1818:
1816:3β-Androstenol
1813:
1811:3α-Androstenol
1801:
1800:
1795:
1790:
1785:
1780:
1775:
1770:
1765:
1760:
1755:
1753:3α-Androstenol
1750:
1741:
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1683:Corticosterone
1680:
1675:
1670:
1665:
1660:
1655:
1646:
1645:
1640:
1627:
1625:
1619:
1618:
1615:
1614:
1612:
1611:
1606:
1601:
1596:
1587:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1545:
1543:
1537:
1536:
1534:
1533:
1519:
1514:
1509:
1504:
1499:
1494:
1489:
1484:
1479:
1474:
1469:
1464:
1459:
1454:
1445:
1444:
1439:
1434:
1429:
1424:
1419:
1414:
1409:
1404:
1399:
1390:
1389:
1387:16-Ketoestrone
1384:
1379:
1374:
1369:
1364:
1359:
1354:
1349:
1344:
1339:
1334:
1329:
1324:
1319:
1314:
1309:
1304:
1299:
1294:
1285:
1283:
1277:
1276:
1274:
1273:
1268:
1263:
1258:
1253:
1248:
1243:
1238:
1233:
1228:
1223:
1218:
1213:
1208:
1203:
1198:
1193:
1188:
1179:
1178:
1173:
1168:
1163:
1158:
1153:
1148:
1143:
1138:
1133:
1128:
1123:
1118:
1116:Androstenediol
1113:
1108:
1103:
1098:
1093:
1087:
1085:
1076:
1070:
1069:
1066:
1065:
1063:
1062:
1057:
1055:Corticosterone
1052:
1047:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1006:
1004:
998:
997:
995:
994:
989:
980:
979:
974:
969:
964:
959:
954:
949:
947:Corticosterone
944:
939:
934:
929:
924:
919:
914:
908:
906:
897:
891:
890:
888:
887:
882:
877:
872:
867:
862:
857:
848:
839:
833:
831:
825:
824:
816:
814:
813:
806:
799:
791:
783:
782:
761:(3): 183–190.
741:
690:
655:
601:
574:
529:
528:
526:
523:
522:
521:
516:
511:
506:
501:
496:
489:
486:
445:
442:
378:glucocorticoid
369:
366:
351:18-Oxocortisol
346:
343:
342:
337:
333:standard state
330:
327:
326:
321:
318:
315:
314:
310:
309:
303:
297:
296:
293:
287:
281:
276:
271:
268:
267:
263:
262:
260:
259:
256:
248:
247:
246:
243:
242:
240:
239:
235:
232:
231:
223:
222:
221:
218:
217:
215:
214:
206:
204:
192:
189:
188:
186:
185:
177:
175:
167:
164:
163:
161:
160:
152:
150:
144:
143:
141:
140:
132:
130:
124:
123:
121:
120:
112:
110:
103:
100:
99:
97:
96:
88:
86:
81:
78:
77:
73:
72:
41:
35:
34:
30:
29:
13:
10:
9:
6:
4:
3:
2:
1946:
1935:
1932:
1930:
1927:
1925:
1922:
1921:
1919:
1904:
1901:
1899:
1896:
1894:
1891:
1889:
1886:
1883:
1882:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1855:
1854:
1852:
1848:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1812:
1809:
1807:
1803:
1802:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1743:
1742:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1651:
1648:
1647:
1644:
1641:
1639:
1637:
1632:
1629:
1628:
1626:
1624:
1623:Neurosteroids
1620:
1610:
1609:Pregnanetriol
1607:
1605:
1602:
1600:
1597:
1595:
1592:
1589:
1588:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1547:
1546:
1544:
1542:
1538:
1531:
1527:
1523:
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1447:
1446:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1425:
1423:
1420:
1418:
1415:
1413:
1410:
1408:
1405:
1403:
1400:
1398:
1395:
1392:
1391:
1388:
1385:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1353:
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1335:
1333:
1330:
1328:
1325:
1323:
1320:
1318:
1315:
1313:
1312:17α-Estradiol
1310:
1308:
1305:
1303:
1300:
1298:
1295:
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1199:
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733:
728:
723:
718:
713:
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694:
691:
686:
682:
678:
674:
671:(6): 335–41.
670:
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659:
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651:
647:
642:
637:
633:
629:
625:
621:
617:
610:
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413:dexamethasone
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367:
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328:
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45:
40:
36:
31:
27:
22:
16:
1884:
1856:
1836:Androsterone
1831:Androstenone
1804:
1793:DHEA sulfate
1783:Androsterone
1745:Androstanes:
1744:
1728:Progesterone
1718:Pregnenolone
1713:Pregnanolone
1649:
1635:
1631:Cholestanes:
1630:
1599:Pregnanediol
1591:Metabolites:
1590:
1549:Progesterone
1541:Progestogens
1449:Metabolites:
1448:
1427:DHEA sulfate
1393:
1288:
1183:Metabolites:
1182:
1176:Testosterone
1141:DHEA sulfate
1126:Androsterone
1074:Sex steroids
984:Metabolites:
983:
977:Progesterone
972:Pregnenolone
860:Pregnenolone
852:
843:
758:
754:
744:
707:
703:
693:
668:
664:
658:
626:(1): R1–R9.
623:
619:
587:
583:
577:
553:(3): 881–9.
550:
546:
474:synthesizing
447:
444:Biosynthesis
417:
386:biosynthesis
371:
350:
349:
76:Identifiers
67:
63:
59:
55:
51:
47:
43:
15:
1758:7-Keto-DHEA
1643:Cholesterol
1432:7-Keto-DHEA
1050:Aldosterone
837:Cholesterol
710:(1): 3–13.
478:aldosterone
429:aldosterone
266:Properties
137:CHEBI:89213
1918:Categories
1873:Calcitriol
1806:Pheromones
1650:Pregnanes:
829:Precursors
818:Endogenous
704:Gland Surg
525:References
404:increases
355:endogenous
301:Molar mass
148:ChemSpider
104:3D model (
83:CAS Number
39:IUPAC name
1924:Pregnanes
1858:Vitamin D
1297:Estradiol
1289:Estranes:
1281:Estrogens
1083:Androgens
957:Cortisone
409:excretion
93:2410-60-8
1929:Steroids
1584:5α-DHDOC
1292:Estetrol
1060:Cortisol
952:Cortisol
821:steroids
777:27853054
736:32206594
685:27219889
650:28904009
596:20963880
569:22238407
494:Cortisol
488:See also
398:adenomas
374:diseases
362:cortisol
157:24840619
1885:Others:
1524:(e.g.,
1394:Others:
1307:Estriol
1302:Estrone
727:7082274
641:5705277
462:CYP11B2
458:CYP11B1
437:CACNA1D
406:urinary
358:steroid
306:376.449
169:PubChem
1850:Others
851:20α,22
775:
734:
724:
683:
648:
638:
594:
567:
353:is an
250:SMILES
182:123712
33:Names
1738:THDOC
1693:DHDOC
433:KCNJ5
225:InChI
128:ChEBI
106:JSmol
1788:DHEA
1422:DHEA
1136:DHEA
773:PMID
732:PMID
681:PMID
646:PMID
592:PMID
565:PMID
480:and
470:ACTH
460:and
435:and
1733:THB
1688:DHC
763:doi
759:240
722:PMC
712:doi
673:doi
669:124
636:PMC
628:doi
624:178
555:doi
380:or
199:EPA
172:CID
66:,17
62:,14
58:,13
54:,11
50:,10
1920::
1634:24
1528:,
842:22
771:.
757:.
753:.
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706:.
702:.
679:.
667:.
644:.
634:.
622:.
618:.
604:^
588:68
563:.
551:97
549:.
545:.
533:^
484:.
400:.
364:.
288:28
282:21
46:,9
42:(8
1860::
1808::
1636:S
1532:)
853:R
844:R
810:e
803:t
796:v
779:.
765::
738:.
714::
708:9
687:.
675::
652:.
630::
598:.
571:.
557::
294:6
291:O
285:H
279:C
201:)
197:(
108:)
68:R
64:S
60:R
56:S
52:R
48:S
44:S
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