3-[4-(methoxycarbonyl)-4-(N-phenylpropanamido)piperidin-1-yl]propanoic acid

• ChemBase ID: 177392
• Molecular Formular: C19H26N2O5
• Molecular Mass: 362.42014
• Monoisotopic Mass: 362.18417194
• SMILES: c1ccc(cc1)N(C1(CCN(CC1)CCC(=O)O)C(=O)OC)C(=O)CC
• Canonical SMILES: COC(=O)C1(CCN(CC1)CCC(=O)O)N(c1ccccc1)C(=O)CC
• InChI: InChI=1S/C19H26N2O5/c1-3-16(22)21(15-7-5-4-6-8-15)19(18(25)26-2)10-13-20(14-11-19)12-9-17(23)24/h4-8H,3,9-14H2,1-2H3,(H,23,24)
• InChIKey: GFJKFSFFMHOISI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[4-(methoxycarbonyl)-4-(N-phenylpropanamido)piperidin-1-yl]propanoic acid
• IUPAC Traditional name: 3-[4-(methoxycarbonyl)-4-(N-phenylpropanamido)piperidin-1-yl]propanoic acid
• Synonyms: 4-(Methoxycarbonyl)-4-[(1-oxopropyl)phenylamino]-1-piperidinepropanoic Acid; GI 90291; GR 90291; Remifentanil Acid

Database IDs

• CAS Number: 132875-68-4
• PubChem SID: 164233302
• PubChem CID: 131560

CALCULATED PROPERTIES

• Acid pKa: 2.9408817
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.3573372
• LogD (pH = 7.4): -1.4212314
• Log P: -1.3586388
• Molar Refractivity: 95.7924 cm^3
• Polarizability: 37.576885 Å^3
• Polar Surface Area: 87.15 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R143520

A metabolite of Remifentanil.

REFERENCES

• Hoke, J., et al.: J. Pharmacol. Exp. Ther., 281, 226 (1997)
• Bender, J., et al.: J. Pharm. Biomed. Anal., 21, 559 (1997)
• Manullang, J., et al.: Anesth. Analg., 89, 529 (1997)