cyclopamine-KAAD   Click here for help

GtoPdb Ligand ID: 10329

Synonyms: 3-keto, N-aminoethyl aminocaproyl dihydrocinnamoyl cyclopamine | KAAD-cyclopamine
Compound class: Synthetic organic
Comment: Cyclopamine-KAAD is a synthetic derivative of the plant-derived teratogen and SMO antagonist cyclopamine [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 87.74
Molecular weight 697.48
XLogP 5.27
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CC1CN(CCNC(=O)CCCCCNC(=O)CCc2ccccc2)C2C(C1)OC1(C2C)CCC2C(=C1C)CC1C2CC=C2C1(C)CCC(=O)C2
Isomeric SMILES CC1CN(CCNC(=O)CCCCCNC(=O)CCc2ccccc2)C2C(C1)OC1(C2C)CCC2C(=C1C)CC1C2CC=C2C1(C)CCC(=O)C2
InChI InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)18-20-43(33,4)38(36)27-37(35)30(44)2/h5,7-8,11-12,15,29,31,35-36,38-39,42H,6,9-10,13-14,16-28H2,1-4H3,(H,45,50)(H,46,49)
InChI Key WDHRPWOAMDJICD-UHFFFAOYSA-N
References
1. Taipale J, Chen JK, Cooper MK, Wang B, Mann RK, Milenkovic L, Scott MP, Beachy PA. (2000)
Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine.
Nature, 406 (6799): 1005-9. [PMID:10984056]