(2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetic acid

• ChemBase ID: 164902
• Molecular Formular: C15H14ClNO2S
• Molecular Mass: 307.79516
• Monoisotopic Mass: 307.04337737
• SMILES: c12c(CCN(C1)[C@@H](c1c(cccc1)Cl)C(=O)O)scc2
• Canonical SMILES: OC(=O)[C@H](c1ccccc1Cl)N1CCc2c(C1)ccs2
• InChI: InChI=1S/C15H14ClNO2S/c16-12-4-2-1-3-11(12)14(15(18)19)17-7-5-13-10(9-17)6-8-20-13/h1-4,6,8,14H,5,7,9H2,(H,18,19)/t14-/m0/s1
• InChIKey: DCASRSISIKYPDD-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetic acid
• IUPAC Traditional name: (S)-(2-chlorophenyl)(4H,6H,7H-thieno[3,2-c]pyridin-5-yl)acetic acid
• Synonyms: (S)-α-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic Acid; SR 26334; Clopidogrel Carboxylic Acid; (R)-α-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic Acid; R-Clopidogrel Carboxylic Acid

Database IDs

• CAS Number: 324757-50-8; 144457-28-3
• PubChem SID: 162259036
• PubChem CID: 9861403

CALCULATED PROPERTIES

• Acid pKa: 1.8096216
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.2264116
• LogD (pH = 7.4): 1.1270517
• Log P: 1.2272639
• Molar Refractivity: 80.1579 cm^3
• Polarizability: 30.900764 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid; Pale Yellow Solid
• Melting Point: 137-141°C; 139-141°C

Safety Information

• Storage Condition: -20°C Freezer; Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C587240

A metabolite of the drug Clopidogrel.

Toronto Research Chemicals - C587230

An optically active metabolite of the drug Clopidogrel.

REFERENCES

• Savi, P., et al.: Biochem. Pharmacol., 44, 527 (1992)
• Pereillo, J., et al.: Drug Metab. Dispos., 30, 1288 (1992)
• Ksycinska, H., et al.: J. Pharm. Biomed. Anal., 41, 533 (1992)
• Farid, N., et al.: Clin. Pharmacol. Ther., 81, 735 (1992)