2-[(3Z)-1-[1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid

• ChemBase ID: 164914
• Molecular Formular: C16H18ClNO4S
• Molecular Mass: 355.83642
• Monoisotopic Mass: 355.06450674
• SMILES: c1ccc(c(c1)C(N1CCC(/C(=C\C(=O)O)/C1)S)C(=O)OC)Cl
• Canonical SMILES: COC(=O)C(c1ccccc1Cl)N1CCC(/C(=C\C(=O)O)/C1)S
• InChI: InChI=1S/C16H18ClNO4S/c1-22-16(21)15(11-4-2-3-5-12(11)17)18-7-6-13(23)10(9-18)8-14(19)20/h2-5,8,13,15,23H,6-7,9H2,1H3,(H,19,20)/b10-8-
• InChIKey: CWUDNVCEAAXNQA-NTMALXAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3Z)-1-[1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid
• IUPAC Traditional name: [(3Z)-1-[1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid
• Synonyms: (3Z)-3-(Carboxymethylene)-α-(2-chlorophenyl)-4-mercapto-1-piperidineacetic Acid 1-Methyl Ester; cis-Clopidogrel Thiol Metabolite(Mixture of Diastereomers)Discontinued

Database IDs

• PubChem SID: 162259048
• PubChem CID: 15462958

CALCULATED PROPERTIES

• Acid pKa: 3.8808222
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.83086616
• LogD (pH = 7.4): -0.54973465
• Log P: 0.9839579
• Molar Refractivity: 91.1839 cm^3
• Polarizability: 35.55107 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C587270

Cis-isomer of the active metabolite of Clopidogrel (C587250).

REFERENCES

• Savi, P., et al.: Biochem. Pharmacol., 44, 527 (1992)
• Herbert, J., et al.: Cardiovasc. Drug Rev., 11, 180 (1992)
• Sugidachi, A., et al.: B. J. Pharmacol., 132, 47 (1992)
• Pearce, R., et al.: Drug Metab. Dispos., 34, 1035 (1992)