(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid

• ChemBase ID: 128924
• Molecular Formular: C13H16N2O4
• Molecular Mass: 264.27714
• Monoisotopic Mass: 264.111007
• SMILES: O=C(N[C@H](C(=O)O)CCC(=O)N)Cc1ccccc1
• Canonical SMILES: O=C(Cc1ccccc1)N[C@H](C(=O)O)CCC(=O)N
• InChI: InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1
• InChIKey: JFLIEFSWGNOPJJ-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid
• IUPAC Traditional name: phenylacetylglutamine
• Synonyms: Phenylacetylglutamine; N2-(2-Phenylacetyl)-L-glutamine; N-Phenylacetylglutamine; N2-(Phenylacetyl)-L-glutamine; NSC 203800; Phenylacetyl-L-glutamine; Phenylacetylglutamine; Phenylacetyl L-Glutamine

Database IDs

• CAS Number: 28047-15-6
• PubChem SID: 162223226
• PubChem CID: 92258
• CHEBI ID: 17884
• Chemspider ID: 83292
• Wikipedia Title: Phenylacetylglutamine

CALCULATED PROPERTIES

• Acid pKa: 3.8975413
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.6936885
• LogD (pH = 7.4): -3.3004804
• Log P: -0.08561821
• Molar Refractivity: 67.2756 cm^3
• Polarizability: 26.210003 Å^3
• Polar Surface Area: 109.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 115-119°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - P306500

It is used as biomarker for metabolic age.

REFERENCES

• Selmer, T., et al.: Eur. J. Biochem., 268, 1363 (2001)
• Connelly, J., et al.: Drug Metab. Dispos., 30, 1357 (2001)
• Lindon, J., et al.: Pharm. Res., 23, 1075 (2001)
• Monteagudo, E., et al.: Xenobiotica, 37, 1000 (2001)