docetaxel   Click here for help

GtoPdb Ligand ID: 6809

Synonyms: Docecad® | docetaxel anhydrous | EmDOC | Taxotere®
Approved drug PDB Ligand
docetaxel is an approved drug (FDA (1996), EMA (1995))
Compound class: Synthetic organic
Comment: Docetaxel is a pan tubulin inhibitor which is a semi-synthetic analogue of paclitaxel (taxol), an extract from the bark of the rare Pacific yew tree Taxus brevifolia.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: docetaxel

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 15
Hydrogen bond donors 5
Rotatable bonds 14
Topological polar surface area 224.45
Molecular weight 807.35
XLogP 2.4
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(=O)OC12COC1CC(C1(C2C(OC(=O)c2ccccc2)C2(O)CC(OC(=O)C(C(c3ccccc3)NC(=O)OC(C)(C)C)O)C(=C(C2(C)C)C(C1=O)O)C)C)O
Isomeric SMILES CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](c3ccccc3)NC(=O)OC(C)(C)C)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
InChI InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1
InChI Key ZDZOTLJHXYCWBA-VCVYQWHSSA-N
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
tubulin beta class I Primary target of this compound Hs Inhibitor Inhibition - - -