cyclopamine   Click here for help

GtoPdb Ligand ID: 10328

Synonyms: 11-Deoxyjervine
PDB Ligand
Compound class: Natural product
Comment: Cyclopamine is a SMO antagonist that acts as a potent inhibitor of the Hedgehog (Hh) signaling pathway [1]. It is a natural product present in the roots and rhizomes of Veratrum californicum (corn lily). Multiple structures with alternative stereochemistry are recorded in online chemistry resources.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 41.49
Molecular weight 411.31
XLogP 3.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC1CCC2(C(=CCC3C2CC2=C(C)C4(CCC32)OC2C(C4C)NCC(C2)C)C1)C
Isomeric SMILES O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC2=C(C)[C@]4(CC[C@@H]32)O[C@H]2[C@H]([C@H]4C)NC[C@H](C2)C)C1)C
InChI InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
InChI Key QASFUMOKHFSJGL-LAFRSMQTSA-N
Classification Click here for help
Compound class Natural product
Synonyms Click here for help
11-Deoxyjervine
Database Links Click here for help
Specialist databases
GPCRdb Ligand cyclopamine
Other databases
BindingDB Ligand 50232973
ChEMBL Ligand CHEMBL254129
GtoPdb PubChem SID 381745009
PubChem CID 442972
RCSB PDB Ligand CY8
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UniChem Connectivity Search for chemical match using the InChIKey QASFUMOKHFSJGL-LAFRSMQTSA-N

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Tocris
Cyclopamine (links to external site)
Cat. No. 1623