2-[(2S)-2-[(2H5)benzyl]-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid

• ChemBase ID: 159752
• Molecular Formular: C25H32N2O4
• Molecular Mass: 424.53258
• Monoisotopic Mass: 424.23620751
• SMILES: [C@H]1([C@@](CCN(C1)C[C@@H](C(=O)NCC(=O)O)Cc1ccccc1)(c1cc(ccc1)O)C)C
• Canonical SMILES: OC(=O)CNC(=O)[C@@H](Cc1ccccc1)CN1CC[C@@]([C@H](C1)C)(C)c1cccc(c1)O
• InChI: InChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1
• InChIKey: UPNUIXSCZBYVBB-JVFUWBCBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S)-2-[(^2H₅)benzyl]-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid
• IUPAC Traditional name: [(2S)-2-[(^2H₅)benzyl]-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid
• Synonyms: rac-N-[2-[[4-(3-Hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-(phenyl-d5)propyl]glycine; ADL 8-2698-d5; LY 246736-d5; Entereg-d5; Alvimopan-d5

Database IDs

• CAS Number: 1217616-62-0
• PubChem SID: 162253887
• PubChem CID: 25224670

CALCULATED PROPERTIES

• Acid pKa: 3.7093873
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.81727153
• LogD (pH = 7.4): 0.8211437
• Log P: 0.82215357
• Molar Refractivity: 120.5593 cm^3
• Polarizability: 46.92617 Å^3
• Polar Surface Area: 89.87 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A575802

Labelled Alvimopan. A peripheral μ-opioid receptor antagonist. Gastroprokinetic.

REFERENCES

• Zimmerman, D.M., et al.: J. Med. Chem., 37, 2262 (1994)
• Liu, S.S., et al.: Clin. Pharmacol. Ther., 68, 66 (1994)
• Taguchi, A., et al.: N. Engl. J. Med., 345, 935 (1994)