Jervine

Jervine

Names
IUPAC name (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b- Hexadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-spiro[9H-benzo[a]fluorene- 9,2'(3'H)-furo[3,2-b] pyridin]-11(1H)-one
Other names (3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
Identifiers
CAS Number	469-59-0 N
3D model (Jmol)	Interactive image
ChemSpider	9694 Y
ECHA InfoCard	100.006.745
PubChem CID	10098
InChI InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1 Y Key: CLEXYFLHGFJONT-DNMILWOZSA-N Y InChI=1/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1 Key: CLEXYFLHGFJONT-DNMILWOZBJ
SMILES O=C5/C3=C(/[C@@]1(O[C@@H]2C[C@@H](CN[C@H]2[C@H]1C)C)CC[C@H]3[C@@H]6C/C=C4/C[C@@H](O)CC[C@]4(C)[C@@H]56)C
Properties
Chemical formula	C27H39NO3
Molar mass	425.60 g/mol
Solubility	10 mg/mL in EtOH 6 mg/mL in DMF
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Jervine is a steroidal alkaloid with molecular formula C₂₇H₃₉NO₃ which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.

Jervine is a potent teratogen causing birth defects in vertebrates. In severe cases it can cause cyclopia and holoprosencephaly.

Jervine's biological activity is mediated via its interaction with the 7 pass trans membrane protein smoothened. Jervine binds with and inhibits smoothened, which is an integral part of the hedgehog signaling pathways. With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.