2-(3-phenylpropanamido)acetic acid

• ChemBase ID: 176637
• Molecular Formular: C11H13NO3
• Molecular Mass: 207.22582
• Monoisotopic Mass: 207.08954328
• SMILES: C(NC(=O)CCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(NCC(=O)O)CCc1ccccc1
• InChI: InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)
• InChIKey: YEIQSAXUPKPPBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-phenylpropanamido)acetic acid
• IUPAC Traditional name: phenylpropionylglycine
• Synonyms: N-(1-oxo-3-phenylpropyl)glycine; (3-Phenylpropionyl)glycine; N-(3-Phenylpropanoyl)glycine; N-(3-Phenylpropionyl)glycine

Database IDs

• CAS Number: 56613-60-6
• PubChem SID: 164232547
• PubChem CID: 152323

CALCULATED PROPERTIES

• Acid pKa: 4.002246
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.5570475
• LogD (pH = 7.4): -2.2075014
• Log P: 0.95027953
• Molar Refractivity: 54.7701 cm^3
• Polarizability: 21.275677 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P336210

N-(3-Phenylpropionyl)glycine detection is a useful diagnostic tool in the diagnosis of many organic acidemias and mitochondrial fatty acid β-oxidation defects. N-(3-Phenylpropionyl)glycine is present in the urine of medium-chain acyl-CoA dehydrogenase def

REFERENCES

• Duran, M. et al.: Prog. Clin. Biol. Res., 321, 419 (1988)
• Bonafe, L. et al.: Mol. Gen. Metab., 69, 311 (1988)
• Ombrone, D. et al.: Anal. Biochem., 417, 122 (1988)