paclitaxel   Click here for help

GtoPdb Ligand ID: 2770

Synonyms: 7-epipaclitaxel | Abraxane® (albumin-bound suspension) | Taxol®
Approved drug PDB Ligand
paclitaxel is an approved drug (FDA (1992), EMA (2008))
Comment: Paclitaxel is a tubulin inhibitor. It was originally identified and isolated from the bark of the Pacific yew, Taxus brevifolia (hence the name 'taxol', and naming of the taxane family of compounds- includes docetaxel and cabazitaxel). The drug can be administered as a solvent-based drug, or in a formulation called nab-paclitaxel. Nab-paclitaxel consists of paclitaxel bound to albumin nanoparticles as a delivery vehicle (trade name Abraxane)- nab stands for nanoparticle albumin-bound.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 221.29
Molecular weight 853.33
XLogP 2.96
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)OC1C(=O)C2(C)C(O)CC3C(C2C(C2(C(C1=C(C)C(OC(=O)C(C(c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
Isomeric SMILES CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
InChI InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChI Key RCINICONZNJXQF-MZXODVADSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1992), EMA (2008))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
International Nonproprietary Names Click here for help
INN number INN
7052 paclitaxel
Synonyms Click here for help
7-epipaclitaxel | Abraxane® (albumin-bound suspension) | Taxol®
Database Links Click here for help
BindingDB Ligand 50001839
CAS Registry No. 33069-62-4 (source: Scifinder)
ChEBI CHEBI:45863
ChEMBL Ligand CHEMBL428647
DrugBank Ligand DB01229
DrugCentral Ligand 2044
GtoPdb PubChem SID 135652721
PubChem CID 36314
RCSB PDB Ligand TA1
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Wikipedia Paclitaxel