2-Oxoclopidogrel (CHEM022004)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:17:46 UTC
Update Date2016-11-09 01:17:24 UTC
Accession NumberCHEM022004
Identification
Common Name2-Oxoclopidogrel
ClassSmall Molecule
Description2-Oxoclopidogrel is a thiolactone intermediate of clopidogrel, an antithrombotic prodrug (PMID: 23249383).. Hepatic cytochrome P450 (P450) enzymes catalyze the conversion of clopidogrel to 2-oxo-clopidogrel via CYP3A oxidation. After oxidation, 2-oxoclopidogrel is then subsequently hydrolyzed to the clopidogrel active metabolite known as CAM (PMID: 25970225). 2-oxoclopidogrel can form four isomers (H1, H2, H3 and H4) of CAM, in which H4 only found in humans. The H4 isomer exhibits twice the activity of the H2 isomer (PMID: 28602635). The H4 isomer blocks adenosine diphosphate (ADP) binding to the P2Y12 receptor which thereby inhibits ADP induced platelet aggregation. 2-oxoclopidogrel is only found in individuals that have used or taken Clopidogrel.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-oxo-ClopidogrelHMDB
(2S)Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno(3,2-c)pyridin-5(2H,4H,6H)-yl)acetateHMDB
Chemical FormulaC16H16ClNO3S
Average Molecular Mass337.821 g/mol
Monoisotopic Mass337.054 g/mol
CAS Registry NumberNot Available
IUPAC Namemethyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-2H,4H,5H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate
Traditional Namemethyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-4H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate
SMILESCOC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl
InChI IdentifierInChI=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 KeyJBSAZVIMJUOBNB-WUJWULDRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Thienopyridine
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • Methyl ester
  • Carbothioic s-lactone
  • 2,5-dihydrothiophene
  • Tertiary aliphatic amine
  • Thiocarboxylic acid ester
  • Tertiary amine
  • Carboxylic acid ester
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organohalogen compound
  • Organopnictogen compound
  • Organochloride
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP2.75ALOGPS
logP2.87ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.28ChemAxon
pKa (Strongest Basic)4.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.01 m³·mol⁻¹ChemAxon
Polarizability33.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0190000000-489b988baa99d3ba5ff1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0119000000-8a5e7008cac66b267421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-0196000000-26909a713c5535a89bf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-4590000000-bc0e44783d88160ecf93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-9bddc2d228e1e448d914Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7c-0159000000-6c8164efb2cd0531f5edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-6791000000-0473925e521b6029585bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0049000000-adb4e0342f064419581dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5192000000-e19d0ffa95f84bc89156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9682000000-aef34ebc8a3f6b9a9ce6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-584cee3804a36ce3f821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0229000000-10f9eb47c9a85cda3886Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0944000000-9d423bbf8f92a15c9fd8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013929
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID28518812
ChEBI IDNot Available
PubChem Compound ID56848893
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhu Y, Zhou J: In vitro biotransformation studies of 2-oxo-clopidogrel: multiple thiolactone ring-opening pathways further attenuate prodrug activation. Chem Res Toxicol. 2013 Jan 18;26(1):179-90. doi: 10.1021/tx300460k. Epub 2012 Dec 28.
2. Dansette PM, Levent D, Hessani A, Mansuy D: Bioactivation of clopidogrel and prasugrel: factors determining the stereochemistry of the thiol metabolite double bond. Chem Res Toxicol. 2015 Jun 15;28(6):1338-45. doi: 10.1021/acs.chemrestox.5b00133. Epub 2015 May 21.
3. Lyngby JG, Court MH, Lee PM: Validation of a method for quantitation of the clopidogrel active metabolite, clopidogrel, clopidogrel carboxylic acid, and 2-oxo-clopidogrel in feline plasma. J Vet Cardiol. 2017 Aug;19(4):384-395. doi: 10.1016/j.jvc.2017.03.004. Epub 2017 Jun 9.