jervine

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. __TOC__

Chemical data

Formula: C27H39NO3
Molecular weight: 425.6 g/mol
IUPAC name: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one
SMILES: C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C(=O)C4=C3C)C)O)C)NC1
InChIKey: CLEXYFLHGFJONT-DNMILWOZSA-N
XLogP: 2.9
Polar surface area: 58.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 425.293

Show 4 more facts

found in taxon: Salvia × sylvestris
chemical formula: C₂₇H₃₉NO₃
canonical SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1
isomeric SMILES: C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C(=O)C4=C3C)C)O)C)NC1

Sources (2)

via Wikidata · CC0

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Encyclopedic overview

3 sections

Contents

Physiological effects
Mechanism of action
References

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

Excerpted from Wikipedia’s “jervine” article, available under the CC BY-SA 4.0 licence.