Jervine
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
SMILES	O=C4C1=[C@](C)[C@@]5(O[C@@](C[C@H](C)CN6)([H])[C@@]6([H])[C@H]5C)CC[C@]([H])1[C@]3([H])CC=C2C[C@@H](O)CC[C@@](C)2[C@]34[H]
Properties
Molecular formula	C27H39NO3
Molar mass	425.60 g/mol
Solubility	10 mg/mL in EtOH 6 mg/mL in DMF
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

[edit] Physiological effects

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

[edit] Mechanism of action

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.^[1] With smoothened inhibited, the GLI1 trancription cannot be activated and hedgehog target genes cannot be transcribed.

[edit] References