(2S,3S,4S,5R,6S)-6-{[2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 164904
• Molecular Formular: C21H22ClNO8S
• Molecular Mass: 483.91928
• Monoisotopic Mass: 483.07546535
• SMILES: C(=O)(O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(N1Cc2c(CC1)scc2)c1c(cccc1)Cl
• Canonical SMILES: O=C(C(c1ccccc1Cl)N1CCc2c(C1)ccs2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H22ClNO8S/c22-12-4-2-1-3-11(12)14(23-7-5-13-10(9-23)6-8-32-13)20(29)31-21-17(26)15(24)16(25)18(30-21)19(27)28/h1-4,6,8,14-18,21,24-26H,5,7,9H2,(H,27,28)/t14?,15-,16-,17+,18-,21-/m0/s1
• InChIKey: TUBQAJBXTWIXFX-RTXXPOPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(2-chlorophenyl)-2-{4H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[α-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetate] β-D-Glucopyranuronic Acid; Clopidogrel Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 162259038
• PubChem CID: 71314947

CALCULATED PROPERTIES

• Acid pKa: 3.0215423
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.55040616
• LogD (pH = 7.4): -1.526327
• Log P: -0.014813545
• Molar Refractivity: 112.4565 cm^3
• Polarizability: 44.77801 Å^3
• Polar Surface Area: 136.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol (sparingly)
• Apperance: Pale Yellow Solid
• Melting Point: 161-167°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C587245

A metabolite of Clopidogrel.