2-{[(1S)-1-carboxy-3-methylbutyl]amino}-6-propanoylbenzoic acid

• ChemBase ID: 103784
• Molecular Formular: C16H21NO5
• Molecular Mass: 307.34164
• Monoisotopic Mass: 307.14197278
• SMILES: CCC(=O)c1cccc(N[C@@H](CC(C)C)C(=O)O)c1C(=O)O
• Canonical SMILES: CCC(=O)c1cccc(c1C(=O)O)N[C@H](C(=O)O)CC(C)C
• InChI: InChI=1S/C16H21NO5/c1-4-13(18)10-6-5-7-11(14(10)16(21)22)17-12(15(19)20)8-9(2)3/h5-7,9,12,17H,4,8H2,1-3H3,(H,19,20)(H,21,22)/t12-/m0/s1
• InChIKey: XAPOPSQDCLWKOB-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1S)-1-carboxy-3-methylbutyl]amino}-6-propanoylbenzoic acid
• IUPAC Traditional name: 2-{[(1S)-1-carboxy-3-methylbutyl]amino}-6-propanoylbenzoic acid
• Synonyms: N-([R,S]-2-CARBOXY-3-PHENYLPROPIONYL)-L-LEUCINE

Database IDs

• CAS Number: 102601-55-8
• PubChem SID: 162102936
• PubChem CID: 71299809

CALCULATED PROPERTIES

• Acid pKa: 3.7394917
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.8624506
• LogD (pH = 7.4): -2.3931863
• Log P: 3.3126478
• Molar Refractivity: 82.7898 cm^3
• Polarizability: 30.993189 Å^3
• Polar Surface Area: 103.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 02152832

A potent and highly-specific enkephalinase inhibitor.

REFERENCES

• Fournie-Zaluski, M.C., J. Med. Chem., 26: 60, (1983).