(2S)-2-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl}-3-phenylpropanoic acid

• ChemBase ID: 159577
• Molecular Formular: C23H29NO3
• Molecular Mass: 367.48126
• Monoisotopic Mass: 367.21474379
• SMILES: [C@H]1([C@@](CCN(C1)C[C@H](Cc1ccccc1)C(=O)O)(c1cc(ccc1)O)C)C
• Canonical SMILES: Oc1cccc(c1)[C@]1(C)CCN(C[C@@H]1C)C[C@@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C23H29NO3/c1-17-15-24(12-11-23(17,2)20-9-6-10-21(25)14-20)16-19(22(26)27)13-18-7-4-3-5-8-18/h3-10,14,17,19,25H,11-13,15-16H2,1-2H3,(H,26,27)/t17-,19-,23+/m0/s1
• InChIKey: KSBSLJKYJXTATP-WCAVRKLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl}-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl}-3-phenylpropanoic acid
• Synonyms: (αS,3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoic Acid; [3R-[1(S*),3α,4α]]-4-(3-Hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoic Acid; ADL 08-0011

Database IDs

• CAS Number: 156130-41-5
• PubChem SID: 162253712
• PubChem CID: 9951118

CALCULATED PROPERTIES

• Acid pKa: 3.7487226
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9221146
• LogD (pH = 7.4): 1.9266139
• Log P: 1.927558
• Molar Refractivity: 107.7558 cm^3
• Polarizability: 42.018948 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A291800

ADL 08-0011 is a metabolite of Alvimopan (A575800). Alvimopan amide hydrolized metabolite.

REFERENCES

• Zimmerman, D., et al.: J. Med. Chem., 37, 2262 (1994)
• Kurz, A., et al.: Drugs, 63, 649 (1994)
• Neary, P., et al.: Expert. Opin Invest. Drugs, 4, 479 (1994)