{{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'',3''S'',3′''R'',3′a''S'',6′''S'',6a''S'',6b''S'',7′a''R'',11a''S'',11b''R'')-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(1''H'')-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 = C<sub>27</sub>H<sub>39</sub>NO<sub>3</sub> | MolarMass = 425.60 g/mol | SolubleOther = 10 mg/mL in EtOH<br>6 mg/mL in DMF | Density = | MeltingPt = }} }} {{MCN|date=February 2025}} '''Jervine''' is a steroidal alkaloid with molecular formula C<sub>27</sub>H<sub>39</sub>NO<sub>3</sub> 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}} __TOC__
==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.<ref>{{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}}</ref> With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.{{cn|date=January 2025}}
== References == {{reflist}}
Category:Teratogens Category:Jervines Category:Spiro compounds Category:Secondary alcohols Category:Ketones Category:Oxygen heterocycles Category:Nitrogen heterocycles Category:Plant toxins