2-[(3Z)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-(methylsulfanyl)piperidin-3-ylidene]acetic acid

• ChemBase ID: 177311
• Molecular Formular: C19H22FNO3S
• Molecular Mass: 363.4462832
• Monoisotopic Mass: 363.13044279
• SMILES: c1ccc(c(c1)C(N1CCC(/C(=C\C(=O)O)/C1)SC)C(=O)C1CC1)F
• Canonical SMILES: CSC1CCN(C/C/1=C/C(=O)O)C(c1ccccc1F)C(=O)C1CC1
• InChI: InChI=1S/C19H22FNO3S/c1-25-16-8-9-21(11-13(16)10-17(22)23)18(19(24)12-6-7-12)14-4-2-3-5-15(14)20/h2-5,10,12,16,18H,6-9,11H2,1H3,(H,22,23)/b13-10-
• InChIKey: UUMYYIQRSCXALD-RAXLEYEMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3Z)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-(methylsulfanyl)piperidin-3-ylidene]acetic acid
• IUPAC Traditional name: [(3Z)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-(methylsulfanyl)piperidin-3-ylidene]acetic acid
• Synonyms: 2-[1-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-(methylthio)-3-piperidinylidene]acetic Acid; R 106583; Prasugrel Metabolite M5; R-106583 (Prasugrel Metabolite)

Database IDs

• CAS Number: 916599-27-4
• PubChem SID: 164233221
• PubChem CID: 69553995

CALCULATED PROPERTIES

• Acid pKa: 4.069535
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.2824234
• LogD (pH = 7.4): 0.48876053
• Log P: 1.2795744
• Molar Refractivity: 97.4277 cm^3
• Polarizability: 37.418724 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R070150

R-106583 is the S-methylated analogue of the active metabolite of Prasugrel (P701150), a thienopyridine antiplatelet agent.

REFERENCES

• Asai, F. et al.: Platelets, 17, 209 (2006)
• Farid, N.A. et al.: Drug Metab. Dispos., 35, 1096 (2006)