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Celastrol

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248: 173: 1356: 24: 1088:
Byun JY, Kim MJ, Eum DY, Yoon CH, Seo WD, Park KH, et al. (October 2009). "Reactive oxygen species-dependent activation of Bax and poly(ADP-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid pristimerin in human cervical cancer cells".
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Zhu H, Liu XW, Cai TY, Cao J, Tu CX, Lu W, et al. (August 2010). "Celastrol acts as a potent antimetastatic agent targeting beta1 integrin and inhibiting cell-extracellular matrix adhesion, in part via the p38 mitogen-activated protein kinase pathway".
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Avilla J, Teixidò A, Velázquez C, Alvarenga N, Ferro E, Canela R (January 2000). "Insecticidal activity of Maytenus species (Celastraceae) nortriterpene quinone methides against codling moth, Cydia pomonella (L.) (Lepidoptera: tortricidae)".
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Kyriakou E, Schmidt S, Dodd GT, et al. Celastrol Promotes Weight Loss in Diet-Induced Obesity by Inhibiting the Protein Tyrosine Phosphatases PTP1B and TCPTP in the Hypothalamus. J Med Chem. 2018;61(24):11144-11157.
271:
InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
281:
InChI=1/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
809:
Kim DH, Shin EK, Kim YH, Lee BW, Jun JG, Park JH, Kim JK (September 2009). "Suppression of inflammatory responses by celastrol, a quinone methide triterpenoid isolated from Celastrus regelii".
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Allison AC, Cacabelos R, Lombardi VR, Alvarez XA, Vigo C (October 2001). "Celastrol, a potent antioxidant and anti-inflammatory drug, as a possible treatment for Alzheimer's disease".
520:, which triggers the heat shock response. The available evidence indicates that celastrol bonds covalently to the thiol groups of cysteine residues in its molecular targets. 1268:
Lee JH, Koo TH, Yoon H, Jung HS, Jin HZ, Lee K, Lee JJ (2006). "Inhibition of NF-κB activation through targeting IκB kinase by celastrol, a quinone methide triterpenoid".
465:, anti-inflammatory, anticancer, and insecticidal activities. It has been shown to have obesity-controlling effects in mice by inhibiting negative regulators of 997:"Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo" 297: 532: 262: 854:"Celastrus-derived celastrol suppresses autoimmune arthritis by modulating antigen-induced cellular and humoral effector responses" 75:)-10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid 905:"Celastrol-induced degradation of FANCD2 sensitizes pediatric high-grade gliomas to the DNA-crosslinking agent carboplatin" 387: 205: 1411:"In vitro activity of celastrol in combination with thymol against carbapenem-resistant Klebsiella pneumoniae isolates" 226: 1415: 1374:
Salminen A, Lehtonen M, Paimela T, Kaarniranta K (April 2010). "Celastrol: Molecular targets of Thunder God Vine".
1459: 717:"Antimicrobial Activity and Mode of Action of Celastrol, a Nortriterpen Quinone Isolated from Natural Sources" 1178:
Pfuhlmann K, Schriever SC, Baumann P, Kabra DG, Harrison L, Mazibuko-Mbeje SE, et al. (November 2018).
956:"Enhancement of radiation sensitivity in lung cancer cells by celastrol is mediated by inhibition of Hsp90" 168: 1469: 408: 536: 442:(IL-1). IL1R1 knock-out mice exposed to celastrol exhibit no leptin-sensitizing or anti-obesity effect. 46: 36: 1305:"Celastrol, an NF-κB inhibitor, improves insulin resistance and attenuates renal injury in db/db mice" 1464: 1316: 482: 427: 414: 1474: 903:
Metselaar DS, Meel MH, Benedict B, Waranecki P, Koster J, Kaspers GJL, Hulleman E (November 2019).
243: 96: 1114: 1070: 834: 791: 486: 1484: 1391: 1344: 1285: 1250: 1201: 1150: 1106: 1062: 1026: 977: 936: 885: 826: 783: 748: 697: 648: 597: 566:"SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii" 1434: 1424: 1383: 1334: 1324: 1277: 1240: 1232: 1191: 1142: 1098: 1054: 1016: 1008: 967: 926: 916: 875: 865: 818: 775: 738: 728: 687: 679: 638: 628: 617:"The Orphan Nuclear Receptor 4A1: A Potential New Therapeutic Target for Metabolic Diseases" 587: 577: 320: 150: 214: 106: 1479: 1360: 1355: 423: 247: 172: 1359: This article incorporates text from this source, which is available under the 1320: 995:
Tiedemann RE, Schmidt J, Keats JJ, Shi CX, Zhu YX, Palmer SE, et al. (April 2009).
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Feng X, Guan D, Auen T, Choi JW, Salazar Hernández MA, Lee J, et al. (April 2019).
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3-Hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
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Abdel-Halim MS, Askoura M, Mansour B, Yahya G, El-Ganiny AM (27 September 2022).
1329: 1180:"Celastrol-Induced Weight Loss Is Driven by Hypophagia and Independent From UCP1" 1012: 921: 668:"IL1R1 is required for celastrol's leptin-sensitization and antiobesity effects" 545: 462: 1429: 1387: 1236: 582: 1281: 683: 513: 348: 141: 564:
Ryu YB, Park SJ, Kim YM, Lee JY, Seo WD, Chang JS, et al. (March 2010).
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Lee JH, Choi KJ, Seo WD, Jang SY, Kim M, Lee BW, et al. (March 2011).
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Kim JE, Lee MH, Nam DH, Song HK, Kang YS, Lee JE, et al. (2013).
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Liu J, Lee J, Salazar Hernandez MA, Mazitschek R, Ozcan U (May 2015).
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Except where otherwise noted, data are given for materials in their
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Venkatesha SH, Yu H, Rajaiah R, Tong L, Moudgil KD (April 2011).
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Progress in Neuro-Psychopharmacology & Biological Psychiatry
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signaling via multiple molecular targets: direct inhibition of
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CC1=C(C(=O)C=C2C1=CC=C32(CC4(3(CC5(4C(CC5)(C)C(=O)O)C)C)C)C)O
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Padilla-Montaño N, de León Guerra L, Moujir L (March 2021).
406:) is a chemical compound isolated from the root extracts of 231: 1047:
The Journal of Pharmacology and Experimental Therapeutics
469:. Celastrol has also shown to possess (by inhibition of 418:(Regel's threewingnut). Celastrol is a pentacyclic 615:Zhang L, Wang Q, Liu W, Liu F, Ji A, Li Y (2018). 434:. Also in mice, celastrol increase expression of 430:agonist that alleviates inflammation and induces 193: 105: 8: 570:Bioorganic & Medicinal Chemistry Letters 960:International Journal of Molecular Medicine 1135:Journal of Agricultural and Food Chemistry 811:European Journal of Clinical Investigation 246: 171: 149: 15: 1438: 1428: 1338: 1328: 1244: 1195: 1020: 971: 930: 920: 879: 869: 742: 732: 691: 642: 632: 591: 581: 438:, which is the receptor for the cytokine 213: 556: 457:animal experiments, celastrol exhibits 302: 267: 242: 374:213 °C (415 °F; 486 K) 162: 1221:"Treatment of obesity with celastrol" 274:Key: KQJSQWZMSAGSHN-JJWQIEBTSA-N 7: 858:The Journal of Biological Chemistry 284:Key: KQJSQWZMSAGSHN-JJWQIEBTBS 184: 512:chaperone proteins, inhibition of 14: 1354: 1168:doi:10.1021/acs.jmedchem.8b01224 823:10.1111/j.1365-2362.2009.02186.x 523:Celastrol also has demonstrated 332: 22: 527:inhibitory effects against the 500:and β kinases, inactivation of 384:(at 25 °C , 100 kPa). 338: 326: 1: 780:10.1016/S0278-5846(01)00192-0 422:and belongs to the family of 1330:10.1371/journal.pone.0062068 1013:10.1182/blood-2008-09-179796 922:10.1016/j.ebiom.2019.10.062 516:function and activation of 426:. In mice, celastrol is an 1506: 1430:10.1038/s41429-022-00566-y 1416:The Journal of Antibiotics 1388:10.1016/j.bbrc.2010.03.050 1376:Biochem Biophys Res Commun 1237:10.1016/j.cell.2015.05.011 583:10.1016/j.bmcl.2010.01.152 1282:10.1016/j.bcp.2006.08.014 684:10.1038/s41591-019-0358-x 378: 313: 293: 258: 89: 81: 45: 35: 30: 21: 1270:Biochemical Pharmacology 1059:10.1124/jpet.110.165654 871:10.1074/jbc.M111.226365 485:and improve whole-body 412:(Thunder god vine) and 1103:10.1124/mol.109.056259 1091:Molecular Pharmacology 540:, in combination with 409:Tripterygium wilfordii 973:10.3892/ijmm.2011.601 734:10.3390/foods10030591 537:Klebsiella pneumoniae 47:Systematic IUPAC name 634:10.1155/2018/9363461 483:diabetic nephropathy 420:nortriterpen quinone 415:Tripterygium regelii 1321:2013PLoSO...862068K 492:Celastrol inhibits 356: g·mol 18: 487:insulin resistance 388:Infobox references 364:Crystalline solid 16: 1276:(10): 1311–1321. 1197:10.2337/db18-0146 1190:(11): 2456–2465. 1147:10.1021/jf990008w 396:Chemical compound 394: 393: 227:CompTox Dashboard 131:Interactive image 1497: 1460:Quinone methides 1445: 1444: 1442: 1432: 1406: 1400: 1399: 1371: 1365: 1358: 1352: 1342: 1332: 1300: 1294: 1293: 1265: 1259: 1258: 1248: 1216: 1210: 1209: 1199: 1175: 1169: 1165: 1159: 1158: 1129: 1123: 1122: 1085: 1079: 1078: 1041: 1035: 1034: 1024: 992: 986: 985: 975: 951: 945: 944: 934: 924: 900: 894: 893: 883: 873: 864:(17): 15138–46. 849: 843: 842: 806: 800: 799: 763: 757: 756: 746: 736: 712: 706: 705: 695: 663: 657: 656: 646: 636: 612: 606: 605: 595: 585: 561: 424:quinone methides 355: 340: 334: 328: 321:Chemical formula 251: 250: 235: 233: 217: 197: 186: 175: 164: 153: 133: 109: 26: 19: 1505: 1504: 1500: 1499: 1498: 1496: 1495: 1494: 1450: 1449: 1448: 1408: 1407: 1403: 1373: 1372: 1368: 1302: 1301: 1297: 1267: 1266: 1262: 1231:(5): 999–1011. 1218: 1217: 1213: 1177: 1176: 1172: 1166: 1162: 1131: 1130: 1126: 1087: 1086: 1082: 1043: 1042: 1038: 1007:(17): 4027–37. 994: 993: 989: 953: 952: 948: 902: 901: 897: 851: 850: 846: 808: 807: 803: 765: 764: 760: 714: 713: 709: 672:Nature Medicine 665: 664: 660: 614: 613: 609: 563: 562: 558: 554: 397: 390: 385: 353: 343: 337: 331: 323: 309: 306: 301: 300: 289: 286: 285: 282: 276: 275: 272: 266: 265: 254: 236: 229: 220: 200: 187: 156: 136: 123: 112: 99: 85: 77: 76: 41: 12: 11: 5: 1503: 1501: 1493: 1492: 1487: 1482: 1477: 1472: 1467: 1462: 1452: 1451: 1447: 1446: 1401: 1366: 1295: 1260: 1211: 1170: 1160: 1124: 1080: 1036: 987: 946: 895: 844: 801: 774:(7): 1341–57. 758: 707: 678:(4): 575–582. 658: 621:J Diabetes Res 607: 555: 553: 550: 395: 392: 391: 386: 382:standard state 379: 376: 375: 372: 366: 365: 362: 358: 357: 351: 345: 344: 341: 335: 329: 324: 319: 316: 315: 311: 310: 308: 307: 304: 296: 295: 294: 291: 290: 288: 287: 283: 280: 279: 277: 273: 270: 269: 261: 260: 259: 256: 255: 253: 252: 239: 237: 225: 222: 221: 219: 218: 210: 208: 202: 201: 199: 198: 190: 188: 180: 177: 176: 166: 158: 157: 155: 154: 146: 144: 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203: 196: 192: 191: 189: 183: 179: 178: 174: 170: 167: 165: 163:ECHA InfoCard 160: 159: 152: 148: 147: 145: 143: 140: 139: 132: 128: 127: 125: 121: 116: 115: 108: 104: 103: 101: 98: 94: 93: 88: 80: 74: 70: 66: 62: 58: 54: 48: 44: 38: 34: 29: 25: 20: 1420: 1414: 1404: 1379: 1375: 1369: 1353: 1312: 1308: 1298: 1273: 1269: 1263: 1228: 1224: 1214: 1187: 1183: 1173: 1163: 1141:(1): 88–92. 1138: 1134: 1127: 1094: 1090: 1083: 1050: 1046: 1039: 1004: 1000: 990: 966:(3): 441–6. 963: 959: 949: 912: 909:EBioMedicine 908: 898: 861: 857: 847: 814: 810: 804: 771: 767: 761: 724: 720: 710: 675: 671: 661: 624: 620: 610: 573: 569: 559: 535: 524: 522: 508:, which are 491: 475:hypothalamus 452: 446: 444: 413: 407: 403: 399: 398: 90:Identifiers 82:Other names 72: 68: 64: 60: 56: 52: 1465:Triterpenes 1423:: 679–690. 627:: 9363461. 546:monoterpene 481:effects on 463:antioxidant 361:Appearance 314:Properties 169:100.164.266 1475:Keto acids 1454:Categories 727:(3): 591. 552:References 514:proteasome 404:tripterine 349:Molar mass 215:L8GG98663L 142:ChemSpider 118:3D model ( 107:34157-83-0 97:CAS Number 84:Tripterine 37:IUPAC name 17:Celastrol 1361:CC BY 4.0 915:: 81–92. 839:205291261 494:IKK-NF-κB 432:autophagy 400:Celastrol 1485:Polyenes 1396:20226165 1363:license. 1349:23637966 1309:PLOS ONE 1290:16984800 1255:26000480 1206:30158241 1184:Diabetes 1155:10637057 1111:19574249 1075:25854329 1067:20472666 1031:19096011 982:21249311 941:31735550 890:21402700 831:19549173 796:21569585 788:11513350 753:33799720 702:30833749 653:30013988 602:20167482 525:in vitro 448:in vitro 1440:9640353 1340:3637455 1317:Bibcode 1246:4768733 1119:6541041 1022:3952546 932:6921187 881:3083183 744:7998816 693:7158951 644:6022324 593:7127101 473:in the 454:in vivo 354:450.619 182:PubChem 1480:Enones 1437:  1394:  1347:  1337:  1288:  1253:  1243:  1204:  1153:  1117:  1109:  1073:  1065:  1029:  1019:  980:  939:  929:  888:  878:  837:  829:  794:  786:  751:  741:  700:  690:  651:  641:  600:  590:  542:thymol 467:leptin 298:SMILES 195:122724 151:109405 31:Names 1490:Enols 1115:S2CID 1071:S2CID 1001:Blood 835:S2CID 792:S2CID 721:Foods 510:HSP90 502:CDC37 471:NF-κB 436:IL1R1 428:NR4A1 263:InChI 120:JSmol 1392:PMID 1345:PMID 1286:PMID 1251:PMID 1225:Cell 1202:PMID 1151:PMID 1107:PMID 1063:PMID 1027:PMID 978:PMID 937:PMID 886:PMID 827:PMID 784:PMID 749:PMID 698:PMID 649:PMID 625:2018 598:PMID 544:, a 518:HSF1 504:and 498:IKKα 451:and 206:UNII 71:,14b 67:,14a 63:,12b 1435:PMC 1425:doi 1384:doi 1380:394 1335:PMC 1325:doi 1278:doi 1241:PMC 1233:doi 1229:161 1192:doi 1143:doi 1099:doi 1055:doi 1051:334 1017:PMC 1009:doi 1005:113 968:doi 927:PMC 917:doi 876:PMC 866:doi 862:286 819:doi 776:doi 739:PMC 729:doi 688:PMC 680:doi 639:PMC 629:doi 588:PMC 578:doi 533:CRE 531:of 506:p23 445:In 232:EPA 185:CID 59:,6a 55:,4a 1456:: 1433:. 1421:75 1419:. 1413:. 1390:. 1378:. 1343:. 1333:. 1323:. 1311:. 1307:. 1284:. 1274:72 1272:. 1249:. 1239:. 1227:. 1223:. 1200:. 1188:67 1186:. 1182:. 1149:. 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Index


IUPAC name
Systematic IUPAC name
CAS Number
34157-83-0
JSmol
Interactive image
ChemSpider
109405
ECHA InfoCard
100.164.266
Edit this at Wikidata
PubChem
122724
UNII
L8GG98663L
CompTox Dashboard
DTXSID2040993
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Melting point
standard state
Infobox references
Tripterygium wilfordii
Tripterygium regelii
nortriterpen quinone
quinone methides

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