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Chemical compound From Wikipedia, the free encyclopedia
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.
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Names | |
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IUPAC name
3β-Hydroxy-17β,23β-epoxyveratraman-11-one | |
Systematic IUPAC name
(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-3-Hydroxy-3′,6′,10,11b-tetramethyl-2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11a,11b-hexadecahydro-3′H-spiro[benzo[a]fluorene-9,2′-furo[3,2-b]pyridin]-11(1H)-one | |
Other names
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one | |
Identifiers | |
3D model (JSmol) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.745 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
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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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.[1] With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.
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