cyclopamine   Click here for help

GtoPdb Ligand ID: 10328

Synonyms: 11-Deoxyjervine
PDB Ligand
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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 or derivative
Synonyms Click here for help
11-Deoxyjervine
Database Links Click here for help
BindingDB Ligand 50232973
ChEMBL Ligand CHEMBL254129
GtoPdb PubChem SID 381745009
PubChem CID 442972
RCSB PDB Ligand CY8
Search Google for chemical match using the InChIKey QASFUMOKHFSJGL-LAFRSMQTSA-N
Search Google for chemicals with the same backbone QASFUMOKHFSJGL
Search UniChem for chemical match using the InChIKey QASFUMOKHFSJGL-LAFRSMQTSA-N
Search UniChem for chemicals with the same backbone QASFUMOKHFSJGL

Product suppliers

View disclaimer

Tocris
Cyclopamine
Cat. No. 1623