2-amino-4-(2-aminophenyl)-4-oxo(1,2-13C2)butanoic acid

• ChemBase ID: 172144
• Molecular Formular: C10H12N2O3
• Molecular Mass: 211.19259857
• Monoisotopic Mass: 211.08853682
• SMILES: c1ccc(c(c1)C(=O)C[13CH]([15NH2])[13C](=O)O)N
• Canonical SMILES: O[13C](=O)[13CH](CC(=O)c1ccccc1N)[15NH2]
• InChI: InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/i8+1,10+1,12+1
• InChIKey: YGPSJZOEDVAXAB-SPKMFNSXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-aminophenyl)-4-oxo(1,2-^1^3C₂)butanoic acid
• IUPAC Traditional name: 2-amino-4-(2-aminophenyl)-4-oxo(1,2-^1^3C₂)butanoic acid
• Synonyms: α,2-Diamino-γ-oxobenzenebutanoic Acid-13C2,15N; 3-Anthraniloylalanine-13C2,15N; DL-Kynurenine-13C2,15N; Kynurenin-13C2,15N; rac Kynurenine-13C2,15N

Database IDs

• PubChem SID: 164228054
• PubChem CID: 71749706

CALCULATED PROPERTIES

• Acid pKa: 1.1930897
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9095553
• LogD (pH = 7.4): -1.9180446
• Log P: -1.9081919
• Molar Refractivity: 55.0502 cm^3
• Polarizability: 20.958498 Å^3
• Polar Surface Area: 106.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K661002

A labelled tryptophan metabolite, is a precursor of kynurenic acid, which is an antagonist of N-methyl-aspartate receptor. An amino acid produced in the body from tryptophan.

REFERENCES

• Mitsuhashi, S., et al.: Anal. Chim. Acta, 584, 315 (1990)
• Swartz, K., et al.: J. Neurosci., 10, 2965 (1990)
• Hasegawa, H., et al.: Anal. Bioanal. Chem., 377, 886 (1990)
• Tsai, Y., et al.: Anal. Biochem., 319, 34 (1990)