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}}

References