tipifarnib   Click here for help

GtoPdb Ligand ID: 8025

Synonyms: R-115777 | R115777
PDB Ligand
Compound class: Synthetic organic
Comment: Tipifarnib is a non-peptidomimetic competitive farnesyltransferase inhibitor (FTI) [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 65.84
Molecular weight 488.12
XLogP 6.97
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc(cc1)C(c1cncn1C)(c1ccc2c(c1)c(cc(=O)n2C)c1cccc(c1)Cl)N
Isomeric SMILES Clc1ccc(cc1)[C@](c1cncn1C)(c1ccc2c(c1)c(cc(=O)n2C)c1cccc(c1)Cl)N
InChI InChI=1S/C27H22Cl2N4O/c1-32-16-31-15-25(32)27(30,18-6-9-20(28)10-7-18)19-8-11-24-23(13-19)22(14-26(34)33(24)2)17-4-3-5-21(29)12-17/h3-16H,30H2,1-2H3/t27-/m1/s1
InChI Key PLHJCIYEEKOWNM-HHHXNRCGSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
farnesyltransferase, CAAX box, beta Primary target of this compound Hs Inhibitor Inhibition 9.1 pIC50 - 1,3
pIC50 9.1 (IC50 8.6x10-10 M) [1,3]
Description: Inhibition of [3H]FPP incorporation into biotinylated laminB peptide by farnesyltransferase protein complex