299:
202:
26:
434:
531:
cannot discriminate between the two. It can therefore participate in certain biochemical reactions (for example, 3-dA can trigger the premature termination of mRNA synthesis). By acting as an adenosine analog, cordycepin was found to be the most potent molecular circadian clock resetter out of
876:
Ju D, Zhang W, Yan J, Zhao H, Li W, Wang J, Liao M, Xu Z, Wang Z, Zhou G, Mei L, Hou N, Ying S, Cai T, Chen S, Xie X, Lai L, Tang C, Park N, Takahashi JS, Huang N, Qi X, Zhang EE (6 May 2020). "Chemical perturbations reveal that RUVBL2 regulates the circadian phase in mammals".
547:. Additionally, cordycepin has been shown to display an effect in some types of other cancers, such as lung, renal, colon, and breast cancer. Cordycepin has been shown to reduce viable A549 lung cancer cell populations by 50%.
946:
Kodama E, McCaffrey R, Yusa K, Mitsuya H (February 2000). "Antileukemic activity and mechanism of action of cordycepin against terminal deoxynucleotidyl transferase-positive (TdT+) leukemic cells".
447:
132:
1164:"The Inhibitory Effect of Cordycepin on the Proliferation of MCF-7 Breast Cancer Cells, and Its Mechanism: An Investigation Using Network Pharmacology-Based Analysis"
694:
Zhou X, Luo L, Dressel W, Shadier G, Krumbiegel D, Schmidtke P, Zepp F, Meyer CU (2008). "Cordycepin is an immunoregulatory active ingredient of
Cordyceps sinensis".
139:
338:
981:
Chou S, Lai W, Hong T, Lai J, Tsai S, Chen Y, Yu S, Kao C, Chu R, Ding S, Li T, Shen T (October 2014). "Synergistic property of cordycepin in cultivated
569:
Cordycepin has been shown to have anti-inflammatory qualities, as well as the ability to defend against injury from cerebral ischemia in mice.
1058:"Cordycepin promotes apoptosis in renal carcinoma cells by activating the MKK7-JNK signaling pathway through inhibition of c-FLIPL expression"
1223:"3'-Deoxyadenosine (Cordycepin) Produces a Rapid and Robust Antidepressant Effect via Enhancing Prefrontal AMPA Receptor Signaling Pathway"
731:"Optimizing cultivation of Cordyceps militaris for fast growth and cordycepin overproduction using rational design of synthetic media"
1390:
313:
220:
322:
InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
454:
256:
559:
277:
1125:"Anti-cancer effect and apoptosis induction of cordycepin through DR3 pathway in the human colonic cancer cell HT-29"
1221:
Li B, Hou Y, Zhu M, Bao H, Nie J, Zhang GY, Shan L, Yao Y, Du K, Yang H, Li M, Zheng B, Xu X, Xiao C, Du J (2016).
489:
1395:
1056:
Hwang IH, Oh SY, Jang HJ, Jo E, Joo JC, Lee KB, Yoo HS, Lee MY, Park SJ, Jang IS (2017-10-18). Ahmad A (ed.).
509:
921:
197:
474:
159:
48:
38:
1334:
1400:
1069:
611:
827:
Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S, et al. (2012).
497:
294:
98:
1385:
1315:
1124:
902:
676:
1362:
1354:
1307:
1299:
1260:
1242:
1203:
1185:
1144:
1105:
1087:
1002:
963:
894:
858:
809:
760:
711:
668:
629:
1346:
1291:
1250:
1234:
1193:
1175:
1136:
1095:
1077:
1036:
994:
955:
886:
848:
840:
799:
791:
750:
742:
703:
660:
619:
600:"Cordycepin, a Metabolic Product isolated from Cultures of Cordyceps militaris (Linn.) Link"
366:
265:
179:
298:
201:
1073:
1024:
615:
108:
1335:"Cordycepin protects against cerebral ischemia/reperfusion injury in vivo and in vitro"
1279:
1255:
1222:
1198:
1163:
1100:
1057:
853:
828:
804:
779:
755:
730:
579:
562:, and these effects, similarly to those of imipramine, are dependent on enhancement of
555:
425:
959:
1379:
1319:
906:
647:
Huang S, Liu H, Sun Y, Chen J, Li X, Xu J, Hu Y, Li Y, Deng Z, Zhong S (2018-01-01).
563:
485:
413:
190:
1278:
Tan L, Song X, Ren Y, Wang M, Guo C, Guo D, Gu Y, Li Y, Cao Z, Deng Y (March 2021).
680:
520:
as a means of infecting insect populations, due to cordycepin's biological activity
1162:
Lee D, Lee WY, Jung K, Kwon Y, Kim D, Hwang G, Kim CE, Lee S, Kang K (2019-08-26).
780:"The selective interruption of nucleolar RNA synthesis in HeLa cells by cordycepin"
536:
1350:
1082:
998:
890:
245:
746:
1140:
707:
664:
551:
478:
400:
210:
170:
1358:
1303:
1246:
1189:
1091:
672:
648:
524:
503:
481:
1366:
1311:
1264:
1207:
1148:
1109:
1006:
967:
898:
862:
844:
764:
715:
633:
1238:
813:
795:
540:
1180:
1041:
598:
Cunningham, K. G., Manson, W., Spring, F. S., Hutchinson, S. A. (1950).
1333:
Cheng Z, He W, Zhou X, Lv Q, Xu X, Yang S, Zhao C, Guo L (2011-08-16).
232:
25:
1295:
624:
599:
528:
493:
150:
1025:"Apoptotic effect of cordycepin on A549 human lung cancer cell line"
649:"An effective and convenient synthesis of cordycepin from adenosine"
424:
Except where otherwise noted, data are given for materials in their
829:"Inhibition of polyadenylation reduces inflammatory gene induction"
501:, but can now be produced synthetically. It is also found in other
138:
131:
121:
492:
position with a hydrogen. It was initially extracted from the
282:
1023:
Tuli HS, Kumar G, Sandhu SS, Sharma AK, Kashyap D (2015).
442:
484:, differing from the latter by the replacement of the
729:
Raethong N, Wang H, Nielsen J, Vongsangnak W (2020).
1280:"Anti-inflammatory effects of cordycepin: A review"
550:Cordycepin has been found to produce rapid, robust
219:
1123:Lee SY, Debnath T, Kim SK, Lim BO (October 2013).
735:Computational and Structural Biotechnology Journal
1227:International Journal of Neuropsychopharmacology
244:
107:
985:-mediated apoptosis in human leukemia cells".
8:
418:225.5 °C (437.9 °F; 498.6 K)
778:Siev, M., Weinberg, R., Penman, S. (1969).
297:
200:
178:
17:
1254:
1197:
1179:
1099:
1081:
1040:
852:
803:
754:
623:
264:
69:-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
920:National Cancer Institute (2011-02-02).
696:The American Journal of Chinese Medicine
590:
343:
318:
293:
191:
1018:
1016:
325:Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N
158:
7:
235:
14:
523:Because cordycepin is similar to
1339:European Journal of Pharmacology
432:
384:
378:
24:
428:(at 25 °C , 100 kPa).
879:Science Translational Medicine
390:
372:
1:
960:10.1016/S0006-2952(99)00325-1
346:O1C(CO)O1N2C(N=CN=C3N)=C3N=C2
1351:10.1016/j.ejphar.2011.04.052
1129:Food and Chemical Toxicology
1083:10.1371/journal.pone.0186489
999:10.1016/j.phymed.2014.07.014
891:10.1126/scitranslmed.aba0769
532:several screened compounds.
560:animal models of depression
351:n2c1c(ncnc1n(c2)3O(C3O)CO)N
1417:
1029:Turkish Journal of Biology
922:"Definition of cordycepin"
747:10.1016/j.csbj.2019.11.003
516:Cordycepin is produced in
1141:10.1016/j.fct.2013.07.068
708:10.1142/S0192415X08006387
665:10.1007/s11696-017-0266-9
535:Cordycepin has displayed
422:
359:
334:
309:
91:
75:
47:
37:
32:
23:
1391:Alkaloids found in fungi
948:Biochemical Pharmacology
510:Ophiocordyceps sinensis
84:-ribofuranosyl)adenine
845:10.1261/rna.032391.112
1284:Phytotherapy Research
49:Systematic IUPAC name
796:10.1083/jcb.41.2.510
1239:10.1093/ijnp/pyv112
1181:10.3390/biom9090414
1074:2017PLoSO..1286489H
1042:10.3906/biy-1408-14
983:Cordyceps militaris
926:NCI Drug Dictionary
616:1950Natur.166..949C
507:species as well as
498:Cordyceps militaris
408: g·mol
20:
455:Infobox references
18:
993:(12): 1516–1524.
885:(542): eaba0769.
471:3'-deoxyadenosine
463:Chemical compound
461:
460:
278:CompTox Dashboard
140:Interactive image
133:Interactive image
83:
42:3′-Deoxyadenosine
1408:
1371:
1370:
1330:
1324:
1323:
1296:10.1002/ptr.6890
1290:(3): 1284–1297.
1275:
1269:
1268:
1258:
1218:
1212:
1211:
1201:
1183:
1159:
1153:
1152:
1120:
1114:
1113:
1103:
1085:
1068:(10): e0186489.
1053:
1047:
1046:
1044:
1020:
1011:
1010:
978:
972:
971:
943:
937:
936:
934:
932:
917:
911:
910:
873:
867:
866:
856:
824:
818:
817:
807:
775:
769:
768:
758:
726:
720:
719:
691:
685:
684:
644:
638:
637:
627:
625:10.1038/166949a0
595:
445:
439:
436:
435:
407:
392:
386:
380:
374:
367:Chemical formula
302:
301:
286:
284:
268:
248:
237:
223:
204:
193:
182:
162:
142:
135:
111:
81:
28:
21:
1416:
1415:
1411:
1410:
1409:
1407:
1406:
1405:
1396:Antidepressants
1376:
1375:
1374:
1332:
1331:
1327:
1277:
1276:
1272:
1220:
1219:
1215:
1161:
1160:
1156:
1122:
1121:
1117:
1055:
1054:
1050:
1022:
1021:
1014:
980:
979:
975:
945:
944:
940:
930:
928:
919:
918:
914:
875:
874:
870:
839:(12): 2236–50.
826:
825:
821:
777:
776:
772:
728:
727:
723:
693:
692:
688:
653:Chemical Papers
646:
645:
641:
597:
596:
592:
588:
575:
464:
457:
452:
451:
450: ?)
441:
437:
433:
429:
405:
395:
389:
383:
377:
369:
355:
352:
347:
342:
341:
330:
327:
326:
323:
317:
316:
305:
287:
280:
271:
251:
238:
226:
213:
185:
165:
145:
125:
114:
101:
87:
85:
79:
71:
70:
43:
12:
11:
5:
1414:
1412:
1404:
1403:
1398:
1393:
1388:
1378:
1377:
1373:
1372:
1325:
1270:
1213:
1154:
1115:
1048:
1012:
973:
954:(3): 273–281.
938:
912:
868:
819:
790:(2): 510–520.
770:
721:
686:
659:(1): 149–160.
639:
589:
587:
584:
583:
582:
580:Deoxyadenosine
574:
571:
556:antidepressant
462:
459:
458:
453:
431:
430:
426:standard state
423:
420:
419:
416:
410:
409:
403:
397:
396:
393:
387:
381:
375:
370:
365:
362:
361:
357:
356:
354:
353:
350:
348:
345:
337:
336:
335:
332:
331:
329:
328:
324:
321:
320:
312:
311:
310:
307:
306:
304:
303:
290:
288:
276:
273:
272:
270:
269:
261:
259:
253:
252:
250:
249:
241:
239:
231:
228:
227:
225:
224:
216:
214:
209:
206:
205:
195:
187:
186:
184:
183:
175:
173:
167:
166:
164:
163:
155:
153:
147:
146:
144:
143:
136:
128:
126:
119:
116:
115:
113:
112:
104:
102:
97:
94:
93:
89:
88:
77:
73:
72:
65:)-2-(6-Amino-9
52:
51:
45:
44:
41:
35:
34:
30:
29:
13:
10:
9:
6:
4:
3:
2:
1413:
1402:
1399:
1397:
1394:
1392:
1389:
1387:
1384:
1383:
1381:
1368:
1364:
1360:
1356:
1352:
1348:
1344:
1340:
1336:
1329:
1326:
1321:
1317:
1313:
1309:
1305:
1301:
1297:
1293:
1289:
1285:
1281:
1274:
1271:
1266:
1262:
1257:
1252:
1248:
1244:
1240:
1236:
1233:(4): pyv112.
1232:
1228:
1224:
1217:
1214:
1209:
1205:
1200:
1195:
1191:
1187:
1182:
1177:
1173:
1169:
1165:
1158:
1155:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1119:
1116:
1111:
1107:
1102:
1097:
1093:
1089:
1084:
1079:
1075:
1071:
1067:
1063:
1059:
1052:
1049:
1043:
1038:
1034:
1030:
1026:
1019:
1017:
1013:
1008:
1004:
1000:
996:
992:
988:
987:Phytomedicine
984:
977:
974:
969:
965:
961:
957:
953:
949:
942:
939:
927:
923:
916:
913:
908:
904:
900:
896:
892:
888:
884:
880:
872:
869:
864:
860:
855:
850:
846:
842:
838:
834:
830:
823:
820:
815:
811:
806:
801:
797:
793:
789:
785:
781:
774:
771:
766:
762:
757:
752:
748:
744:
740:
736:
732:
725:
722:
717:
713:
709:
705:
702:(5): 967–80.
701:
697:
690:
687:
682:
678:
674:
670:
666:
662:
658:
654:
650:
643:
640:
635:
631:
626:
621:
617:
613:
610:(4231): 949.
609:
605:
601:
594:
591:
585:
581:
577:
576:
572:
570:
567:
565:
564:AMPA receptor
561:
557:
553:
548:
546:
542:
539:against some
538:
533:
530:
526:
521:
519:
514:
512:
511:
506:
505:
500:
499:
495:
491:
487:
486:hydroxy group
483:
480:
476:
472:
468:
456:
449:
444:
427:
421:
417:
415:
414:Melting point
412:
411:
404:
402:
399:
398:
371:
368:
364:
363:
358:
349:
344:
340:
333:
319:
315:
308:
300:
296:
295:DTXSID1041007
292:
291:
289:
279:
275:
274:
267:
263:
262:
260:
258:
255:
254:
247:
243:
242:
240:
234:
230:
229:
222:
218:
217:
215:
212:
208:
207:
203:
199:
196:
194:
192:ECHA InfoCard
189:
188:
181:
177:
176:
174:
172:
169:
168:
161:
157:
156:
154:
152:
149:
148:
141:
137:
134:
130:
129:
127:
123:
118:
117:
110:
106:
105:
103:
100:
96:
95:
90:
80:9-(3-Deoxy-β-
74:
68:
64:
60:
56:
50:
46:
40:
36:
31:
27:
22:
16:
1345:(1): 20–28.
1342:
1338:
1328:
1287:
1283:
1273:
1230:
1226:
1216:
1171:
1168:Biomolecules
1167:
1157:
1132:
1128:
1118:
1065:
1061:
1051:
1032:
1028:
990:
986:
982:
976:
951:
947:
941:
929:. Retrieved
925:
915:
882:
878:
871:
836:
832:
822:
787:
784:J. Cell Biol
783:
773:
738:
734:
724:
699:
695:
689:
656:
652:
642:
607:
603:
593:
568:
549:
544:
537:cytotoxicity
534:
522:
517:
515:
508:
502:
496:
470:
466:
465:
160:ChEMBL305686
92:Identifiers
76:Other names
66:
62:
58:
54:
15:
1401:Nucleosides
1135:: 439–447.
1035:: 306–311.
931:21 December
566:signaling.
558:effects in
543:cell lines
360:Properties
198:100.000.720
78:Cordycepine
19:Cordycepin
1380:Categories
1174:(9): 414.
586:References
552:imipramine
479:nucleoside
475:derivative
467:Cordycepin
401:Molar mass
266:GZ8VF4M2J8
211:IUPHAR/BPS
171:ChemSpider
120:3D model (
99:CAS Number
39:IUPAC name
1386:Alkaloids
1359:0014-2999
1320:224828245
1304:0951-418X
1247:1461-1457
1190:2218-273X
1092:1932-6203
907:218533423
673:1336-9075
525:adenosine
518:cordyceps
504:Cordyceps
482:adenosine
1367:21554870
1312:33090621
1265:26443809
1208:31454995
1149:23941773
1110:29045468
1062:PLOS ONE
1007:25442260
968:10609556
899:32376767
863:23118416
765:31890138
716:19051361
681:90915876
634:14796634
573:See also
545:in vitro
541:leukemic
1256:4851261
1199:6770402
1101:5646797
1070:Bibcode
854:3504674
814:5783871
805:2107749
756:6926140
741:: 1–8.
612:Bibcode
529:enzymes
527:, some
488:in the
477:of the
473:, is a
448:what is
446: (
406:251.246
233:PubChem
109:73-03-0
1365:
1357:
1318:
1310:
1302:
1263:
1253:
1245:
1206:
1196:
1188:
1147:
1108:
1098:
1090:
1005:
966:
905:
897:
861:
851:
812:
802:
763:
753:
714:
679:
671:
632:
604:Nature
554:-like
494:fungus
443:verify
440:
339:SMILES
151:ChEMBL
33:Names
1316:S2CID
903:S2CID
677:S2CID
469:, or
314:InChI
122:JSmol
1363:PMID
1355:ISSN
1308:PMID
1300:ISSN
1261:PMID
1243:ISSN
1204:PMID
1186:ISSN
1145:PMID
1106:PMID
1088:ISSN
1003:PMID
964:PMID
933:2015
895:PMID
859:PMID
810:PMID
761:PMID
712:PMID
669:ISSN
630:PMID
257:UNII
246:6303
221:4630
180:6064
86:3-dA
1347:doi
1343:664
1292:doi
1251:PMC
1235:doi
1194:PMC
1176:doi
1137:doi
1096:PMC
1078:doi
1037:doi
995:doi
956:doi
887:doi
849:PMC
841:doi
833:RNA
800:PMC
792:doi
751:PMC
743:doi
704:doi
661:doi
620:doi
608:166
578:2'-
283:EPA
236:CID
1382::
1361:.
1353:.
1341:.
1337:.
1314:.
1306:.
1298:.
1288:35
1286:.
1282:.
1259:.
1249:.
1241:.
1231:19
1229:.
1225:.
1202:.
1192:.
1184:.
1170:.
1166:.
1143:.
1133:60
1131:.
1127:.
1104:.
1094:.
1086:.
1076:.
1066:12
1064:.
1060:.
1033:39
1031:.
1027:.
1015:^
1001:.
991:21
989:.
962:.
952:59
950:.
924:.
901:.
893:.
883:12
881:.
857:.
847:.
837:18
835:.
831:.
808:.
798:.
788:41
786:.
782:.
759:.
749:.
739:18
737:.
733:.
710:.
700:36
698:.
675:.
667:.
657:72
655:.
651:.
628:.
618:.
606:.
602:.
513:.
490:3'
382:13
376:10
61:,5
57:,3
53:(2
1369:.
1349::
1322:.
1294::
1267:.
1237::
1210:.
1178::
1172:9
1151:.
1139::
1112:.
1080::
1072::
1045:.
1039::
1009:.
997::
970:.
958::
935:.
909:.
889::
865:.
843::
816:.
794::
767:.
745::
718:.
706::
683:.
663::
636:.
622::
614::
438:N
394:3
391:O
388:5
385:N
379:H
373:C
285:)
281:(
124:)
82:D
67:H
63:S
59:R
55:S
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
