vismodegib   Click here for help

GtoPdb Ligand ID: 6975

Synonyms: Erivedge® | GDC-0449 | HhAntag691
Approved drug PDB Ligand
vismodegib is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Vismodegib inhibits smoothened homolog (SMO), a constituent of the Hedgehog signalling pathway which is essential for proper embryonic development. This pathway is also involved in the maintenance and regeneration of adult tissues by regulating adult stem cells and has been implicated in the development of some cancers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 84.51
Molecular weight 420.01
XLogP 4.54
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1ccc(cc1Cl)S(=O)(=O)C)Nc1ccc(c(c1)c1ccccn1)Cl
Isomeric SMILES O=C(c1ccc(cc1Cl)S(=O)(=O)C)Nc1ccc(c(c1)c1ccccn1)Cl
InChI InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)
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Molecular structure representations generated using Open Babel