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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.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1996)  |  EU EMA (1995)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
International Nonproprietary Names Click here for help
INN number INN
6621 docetaxel
Synonyms Click here for help
Docecad® | docetaxel anhydrous | EmDOC | Taxotere®
Database Links Click here for help
CAS Registry No. 114977-28-5
ChEBI CHEBI:4672
ChEMBL Ligand CHEMBL92
DrugBank Ligand DB01248
DrugCentral Ligand 939
GtoPdb PubChem SID 178103415
PubChem CID 148124
RCSB PDB Ligand TXL
Search Google for chemical match using the InChIKey ZDZOTLJHXYCWBA-VCVYQWHSSA-N
Search Google for chemicals with the same backbone ZDZOTLJHXYCWBA
Search PubMed clinical trials docetaxel
Search PubMed titles docetaxel
Search PubMed titles/abstracts docetaxel
UniChem Compound Search for chemical match using the InChIKey ZDZOTLJHXYCWBA-VCVYQWHSSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZDZOTLJHXYCWBA-VCVYQWHSSA-N
Wikipedia Docetaxel

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MedChemExpress
Docetaxel (links to external site)
Cat. No. HY-B0011