cabazitaxel   Click here for help

GtoPdb Ligand ID: 6798

Synonyms: Jevanta® | taxoid XRP6258 | TXD 258 | XRP-6258
Approved drug
cabazitaxel is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: Cabazitaxel is a pan tubulin inhibitor of the taxane class of compounds.
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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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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 3
Rotatable bonds 16
Topological polar surface area 202.45
Molecular weight 835.38
XLogP 3.01
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 COC1C(=O)C2(C)C(OC)CC3C(C2C(C2(C(C1=C(C)C(OC(=O)C(C(c1ccccc1)NC(=O)OC(C)(C)C)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
Isomeric SMILES CO[C@H]1C(=O)[C@]2(C)[C@@H](OC)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)OC(C)(C)C)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
InChI InChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1
InChI Key BMQGVNUXMIRLCK-OAGWZNDDSA-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. FDA (2010)  |  EMA (2011)
International Nonproprietary Names Click here for help
INN number INN
8967 cabazitaxel
Synonyms Click here for help
Jevanta® | taxoid XRP6258 | TXD 258 | XRP-6258
Database Links Click here for help
CAS Registry No. 183133-96-2
ChEMBL Ligand CHEMBL1201748
DrugBank Ligand DB06772
DrugCentral Ligand 4153
GtoPdb PubChem SID 178103404
PubChem CID 9854073
Search Google for chemical match using the InChIKey BMQGVNUXMIRLCK-OAGWZNDDSA-N
Search Google for chemicals with the same backbone BMQGVNUXMIRLCK
Search PubMed clinical trials cabazitaxel
Search PubMed titles cabazitaxel
Search PubMed titles/abstracts cabazitaxel
UniChem Compound Search for chemical match using the InChIKey BMQGVNUXMIRLCK-OAGWZNDDSA-N
UniChem Connectivity Search for chemical match using the InChIKey BMQGVNUXMIRLCK-OAGWZNDDSA-N
Wikipedia Cabazitaxel

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MedChemExpress
Cabazitaxel (links to external site)
Cat. No. HY-15459