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
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Molecular structure representations generated using Open Babel