jervine
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461783099
| Name = Jervine
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Jervine.png
| ImageSize =
| ImageName =
| IUPACName = 3β-Hydroxy-17β,23β-epoxyveratraman-11-one
| SystematicName = (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
| OtherNames = (3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9694
| PubChem = 10098
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 186779
| 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
| InChIKey = CLEXYFLHGFJONT-DNMILWOZBJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CLEXYFLHGFJONT-DNMILWOZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 469-59-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 19V3ECX465
| 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
}}
| Section2 = {{Chembox Properties
| Formula = C27H39NO3
| MolarMass = 425.60 g/mol
| SolubleOther = 10 mg/mL in EtOH
6 mg/mL in DMF
| Density =
| MeltingPt =
}}
}}
{{MCN|date=February 2025}}
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.{{cn|date=January 2025}}
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Physiological effects
Jervine is a potent teratogen causing birth defects in vertebrates. In severe cases it can cause cyclopia and holoprosencephaly.{{cn|date=January 2025}}
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.{{cite journal |author1=Chen, J |author2=Taipale, J |author3=Cooper, M. | title = Inhibition of Hedgehog Signaling by direct binding of Cyclopamine to Smoothened | journal = Genes Dev. | year = 2002 | volume = 16 | pages = 2743–2748 | pmid = 12414725 | issue = 21 | doi = 10.1101/gad.1025302 | pmc = 187469}} With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.{{cn|date=January 2025}}