becondogrel   Click here for help

GtoPdb Ligand ID: 13802

Synonyms: (4S)-2-Oxoclopidogrel | compound IV-1 [EP3290423B1] [3] | compound of formula I [US2022028976]
Compound class: Synthetic organic
Comment: Becondogrel is the INN for a platelet aggregation inhibitor (WHO proposed INN list 132, Feb 2025). It is a derivative of the irreversible P2Y12 receptor anti-platelet prodrug clopidogrel that has been modified to overcome individual differences in hepatic CYP450 enzyme activity that limit conversion of clopidogrel into its active metabolite [1-2] and conversion to an inactive carboxylic derivative by carboxylesterase 1 (CES1) [4]. Becondogrel is a prodrug that is converted to its active metabolite in vivo.
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 4
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 71.91
Molecular weight 337.82
XLogP 0.71
No. Lipinski's rules broken 0

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 COC(=O)[C@H](C1=C(C=CC=C1)Cl)N2CC[C@H]3C(=CC(=O)S3)C2
Isomeric SMILES COC(=O)[C@H](C1=CC=CC=C1Cl)N2CC[C@H]3C(=CC(=O)S3)C2
InChI InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13-,15-/m0/s1
InChI Key JBSAZVIMJUOBNB-ZFWWWQNUSA-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/)
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel