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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL186779 ;
ChemSpider	9694 ;
ECHA InfoCard	100.006.745
PubChem CID	10098;
UNII	19V3ECX465 ;
CompTox Dashboard (EPA)	DTXSID70895026 ;
	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 Key: CLEXYFLHGFJONT-DNMILWOZSA-N ; 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).
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	Infobox references

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

Physiological effects

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

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 transcription cannot be activated and hedgehog target genes cannot be transcribed.

References

Chen, J; Taipale, J; Cooper, M. (2002). "Inhibition of Hedgehog Signaling by direct binding of Cyclopamine to Smoothened". Genes Dev. 16 (21): 2743–2748. doi:10.1101/gad.1025302. PMC 187469. PMID 12414725.

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[1] Chen, J; Taipale, J; Cooper, M. (2002). "Inhibition of Hedgehog Signaling by direct binding of Cyclopamine to Smoothened". Genes Dev. 16 (21): 2743–2748. doi:10.1101/gad.1025302. PMC 187469. PMID 12414725.