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))
Compound class: Natural product
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
Approved drug? Yes (FDA (1992), EMA (2008))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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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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UniChem Compound Search for chemical match using the InChIKey RCINICONZNJXQF-MZXODVADSA-N
UniChem Connectivity Search for chemical match using the InChIKey RCINICONZNJXQF-MZXODVADSA-N
Wikipedia Paclitaxel