2-[(3E)-1-{2-[(2,2,3,3-2H4)cyclopropyl]-1-(2-fluorophenyl)-2-oxoethyl}-4-sulfanylpiperidin-3-ylidene]acetic acid

• ChemBase ID: 177314
• Molecular Formular: C18H20FNO3S
• Molecular Mass: 349.4197032
• Monoisotopic Mass: 349.11479273
• SMILES: c1ccc(c(c1)C(N1CCC(/C(=C/C(=O)O)/C1)S)C(=O)C1CC1)F
• Canonical SMILES: OC(=O)/C=C/1\CN(CCC1S)C(c1ccccc1F)C(=O)C1CC1
• InChI: InChI=1S/C18H20FNO3S/c19-14-4-2-1-3-13(14)17(18(23)11-5-6-11)20-8-7-15(24)12(10-20)9-16(21)22/h1-4,9,11,15,17,24H,5-8,10H2,(H,21,22)/b12-9+
• InChIKey: ZWUQVNSJSJHFPS-FMIVXFBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3E)-1-{2-[(2,2,3,3-^2H₄)cyclopropyl]-1-(2-fluorophenyl)-2-oxoethyl}-4-sulfanylpiperidin-3-ylidene]acetic acid
• IUPAC Traditional name: [(3E)-1-{2-[(2,2,3,3-^2H₄)cyclopropyl]-1-(2-fluorophenyl)-2-oxoethyl}-4-sulfanylpiperidin-3-ylidene]acetic acid
• Synonyms: (2E)-2-[1-[2-(Cyclopropyl-d4)-1-(2-fluorophenyl)-2-oxoethyl]-4-mercapto-3-piperidinylidene]acetic Acid; trans R-138727-d4, (Prasugrel-d4 Metabolite)(Mixture of Diastereomers)Discontinued

Database IDs

• PubChem SID: 164233224
• PubChem CID: 71751947

CALCULATED PROPERTIES

• Acid pKa: 4.0109057
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.8893301
• LogD (pH = 7.4): 0.06517566
• Log P: 0.8934236
• Molar Refractivity: 92.7767 cm^3
• Polarizability: 35.580124 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R070202

The active labelled stereoselective metabolite of Prasugrel (P701150); inhibits ADP-stimulated thrombo-inflammatory markers of platelet activation: influence of other blood cells, calcium, and aspirin.

REFERENCES

• Ekins, S., et al.: J. Pharmacol. Exp. Ther., 286, 1253 (1998)
• Lamba, V., et al.: J. Pharmacol Exp. Ther., 307, 906 (1998)
• Yoneda, K., et al.: Br. J. Pharmacol., 142, 551 (1998)
• Jakubowski, J., et al.: J. Cardiovasc. Pharmacol., 47, 377 (1998)
• Rehmel,