Jervine
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Names | |
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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
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Other names
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
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Identifiers | |
469-59-0 | |
ChEMBL | ChEMBL186779 |
ChemSpider | 9694 |
Jmol 3D model | Interactive image |
PubChem | 10098 |
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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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verify (what is ?) | |
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.
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
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