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Substance Name: Cyclopamine
RN: 4449-51-8
UNII: ZH658AJ192
InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N

Note

  • Teratogen from Veratrum californicum.

Classification Codes

  • Natural Product
  • Reproductive Effect

Molecular Formula

  • C27-H41-N-O2

Molecular Weight

  • 411.6259
 
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Names and Synonyms

Name of Substance

  • Cyclopamine

Synonyms

  • 11-Deoxojervine
  • 11-Deoxyjervine
  • Cyclopamine
  • HSDB 3505
  • UNII-ZH658AJ192
  • Veratraman-3-ol, 17,23-epoxy-, (3beta,23beta)-

Systematic Names

  • Cyclopamine
  • Jervine, 11-deoxo- (7CI)
  • Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)pyridin)-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
  • Veratraman-3-ol, 17,23-epoxy-, (3-beta,23-beta)- (9CI)

Registry Numbers

CAS Registry Number

  • 4449-51-8

FDA UNII

  • ZH658AJ192

Other Registry Numbers

  • 11051-96-0
  • 26108-61-2

System Generated Number

  • 0004449518

Structure Descriptors

InChI

1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1

InChIKey

QASFUMOKHFSJGL-LAFRSMQTSA-N

Smiles

[C@@]12(C(=C3[C@@H](CC2)[C@H]2[C@H](C3)[C@@]3(C(=CC2)C[C@H](CC3)O)C)C)[C@@H]([C@H]2[C@H](O1)C[C@@H](CN2)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LDLo oral 170mg/kg (170mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 149, Pg. 302, 1975.
mouse LDLo oral 180mg/kg (180mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 149, Pg. 302, 1975.