Showing metabocard for Clopidogrel (BMDB0005011)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:36 UTC
Update Date2020-05-11 20:45:54 UTC
BMDB IDBMDB0005011
Secondary Accession Numbers
  • BMDB05011
Metabolite Identification
Common NameClopidogrel
DescriptionClopidogrel, also known as plavix or isocover, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Clopidogrel is a very strong basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-ClopidogrelChEBI
ClopidogrelumChEBI
PlavixKegg
(+)-(S)-ClopidogrelHMDB
(S)-ClopidogrelHMDB
Clopidogrel bisulfateHMDB
Clopidogrel bisulphateHMDB
IsocoverHMDB
Clopidogrel sandozHMDB
Clopidogrel hydrochlorideHMDB
BMS Brand 1 OF clopidogrel bisulfateHMDB
Clopidogrel napadisilateHMDB
Clopidogrel, (+)(S)-isomerHMDB
BMS Brand 2 OF clopidogrel bisulfateHMDB
Clopidogrel besylateHMDB
IscoverHMDB
Clopidogrel-mephaHMDB
Clopidogrel besilateHMDB
Clopidogrel mephaHMDB
Chemical FormulaC16H16ClNO2S
Average Molecular Weight321.822
Monoisotopic Molecular Weight321.059027158
IUPAC Namemethyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
Traditional Nameclopidogrel
CAS Registry Number113665-84-2
SMILES
[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
InChI KeyGKTWGGQPFAXNFI-HNNXBMFYSA-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
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Methyl ester
  • Thiophene
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.84ALOGPS
logP4.03ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)5.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.93 m³·mol⁻¹ChemAxon
Polarizability33.19 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3980000000-d577843e19cf599f8a0bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0229-0967000000-6c51c479e90818ec703bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0229-0967000000-6c51c479e90818ec703bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2900000000-be6dbedd4a0c4f60d0ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0900000000-6cfdcd4344e312b9152eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0592000000-7840275de971a1c4cd01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0039000000-c8efc33e40006dfa1d04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-0910000000-19b1ace18c36bc486855View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-c7ca4d76836b437c0027View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0230-0935000000-9e8f08289a74a12e1d1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0900000000-240a5f13f03a49f5ab78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0159000000-17a9fe29b343cd5ca501View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022l-0192000000-f551440009ad0c2d2404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-2950000000-aea6a4e495e819b37fdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0059000000-71b4a913e2ab55e93430View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0296000000-023d1bb858121c6c9158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-8940000000-ec8e591212f5c1afd516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0189000000-c0c4fea994ad59c6af4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-5290000000-384f9f4c95308bc8487aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-7790000000-5865fdee9334a4d1d30dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-2bc03219cf962da0b1ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0449000000-3d2799457a93e03f946bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-0920000000-0c740a018e7a5007c257View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Liver
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005011
DrugBank IDDB00758
Phenol Explorer Compound IDNot Available
FooDB IDFDB023584
KNApSAcK IDNot Available
Chemspider ID54632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClopidogrel
METLIN ID3965
PubChem Compound60606
PDB IDNot Available
ChEBI ID37941
References
Synthesis ReferenceBousquet, Andre; Musolino, Andree. Hydroxyacetic ester derivatives, namely (R)-methyl 2-(sulfonyloxy)-2-(chlorophenyl)acetates, preparation method, and use as synthesis intermediates for clopidogrel. PCT Int. Appl. (1999), 35 p
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available