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abiraterone acetate   Click here for help

GtoPdb Ligand ID: 9288

Synonyms: Yonsa® | Zytiga®
Approved drug
abiraterone acetate is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Abiraterone acetate is an ester prodrug of the steroidal drug abiraterone, which acts as an androgen synthesis inhibitor by inhibiting steroid 17alpha-monooxygenase.

abiraterone acetate is commercially available from our sponsors

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 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 39.19
Molecular weight 391.25
XLogP 6.28
No. Lipinski's rules broken 1

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)OC1CCC2(C(=CCC3C2CCC2(C3CC=C2c2cccnc2)C)C1)C
Isomeric SMILES CC(=O)O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC=C2c2cccnc2)C)C1)C
InChI InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1
InChI Key UVIQSJCZCSLXRZ-UBUQANBQSA-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. EU EMA (2011)  |  US FDA (2011)
Is prodrug? Yes
Active form abiraterone
IUPAC Name Click here for help
[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms Click here for help
Yonsa® | Zytiga®
Database Links Click here for help
CAS Registry No. 154229-18-2 (source: PubChem)
ChEMBL Ligand CHEMBL271227
DrugCentral Ligand 4176
GtoPdb PubChem SID 318164807
PubChem CID 9821849
Search Google for chemical match using the InChIKey UVIQSJCZCSLXRZ-UBUQANBQSA-N
Search Google for chemicals with the same backbone UVIQSJCZCSLXRZ
UniChem Compound Search for chemical match using the InChIKey UVIQSJCZCSLXRZ-UBUQANBQSA-N
UniChem Connectivity Search for chemical match using the InChIKey UVIQSJCZCSLXRZ-UBUQANBQSA-N
Wikipedia Abiraterone_acetate

Product suppliers

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MedChemExpress
Abiraterone acetate (links to external site)
Cat. No. HY-75054
Abiraterone acetate (Standard) (links to external site)
Cat. No. HY-75054R