(2R)-2-amino-3-{[(3Z)-3-(carboxymethylidene)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidin-4-yl]disulfanyl}propanoic acid

• ChemBase ID: 177313
• Molecular Formular: C21H25FN2O5S2
• Molecular Mass: 468.5620032
• Monoisotopic Mass: 468.11889213
• SMILES: c1ccc(c(c1)C(N1CCC(/C(=C\C(=O)O)/C1)SSC[C@H](N)C(=O)O)C(=O)C1CC1)F
• Canonical SMILES: OC(=O)/C=C\1/CN(CCC1SSC[C@@H](C(=O)O)N)C(c1ccccc1F)C(=O)C1CC1
• InChI: InChI=1S/C21H25FN2O5S2/c22-15-4-2-1-3-14(15)19(20(27)12-5-6-12)24-8-7-17(13(10-24)9-18(25)26)31-30-11-16(23)21(28)29/h1-4,9,12,16-17,19H,5-8,10-11,23H2,(H,25,26)(H,28,29)/b13-9-/t16-,17?,19?/m0/s1
• InChIKey: AMPOCARAOGXMMH-DGVXAMKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(3Z)-3-(carboxymethylidene)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidin-4-yl]disulfanyl}propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[(3Z)-3-(carboxymethylidene)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidin-4-yl]disulfanyl}propanoic acid
• Synonyms: 3-[[(3Z)-3-(Carboxymethylene)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-piperidinyl]dithio]-L-alanine; R-119251 (Prasugrel Metabolite)(Mixture of Diastereoisomers)

Database IDs

• CAS Number: 239466-86-5
• PubChem SID: 164233223
• PubChem CID: 71751946

CALCULATED PROPERTIES

• Acid pKa: 1.8212743
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.8842695
• LogD (pH = 7.4): -2.9315774
• Log P: -1.8513776
• Molar Refractivity: 119.3915 cm^3
• Polarizability: 46.318787 Å^3
• Polar Surface Area: 120.93 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R070180

R-119251 is an inactive metabolite of Prasugrel (P701150), a thienopyridine antiplatelet agent.

REFERENCES

• Sugidachi, A., et al.: Br. J. Pharmacol., 129, 1439 (2000)
• Asai, F., et al.: Platelets, 17, 209 (2000)
• Farid, N., et al.: Drug Metab. Dispos. 35, 1096 (2000)