2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

• ChemBase ID: 102554
• Molecular Formular: C10H12N2O3
• Molecular Mass: 208.21388
• Monoisotopic Mass: 208.08479225
• SMILES: NC(CC(=O)c1c(N)cccc1)C(=O)O
• Canonical SMILES: OC(=O)C(CC(=O)c1ccccc1N)N
• 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)
• InChIKey: YGPSJZOEDVAXAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
• IUPAC Traditional name: kynurenine; alanine, 3-anthraniloyl-, DL-
• Synonyms: β-Anthraniloyl-L-alanine; L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid; L-KYNURENINE; 2-Amino-3-(2-aminobenzoyl)propionic acid; 2-Amino-4-(2-aminophenyl)-4-oxobutyric acid; DL-Kynurenine; α,2-Diamino-γ-oxobenzenebutanoic Acid; 3-Anthraniloylalanine; DL-Kynurenine; Kynurenin; rac Kynurenine; (S)-Kynurenine; Kynurenine; DL-KYNURENINE SULFATE; 2-氨基-4-(2-氨基苯基)-4-氧代丁酸; 2-氨基-3-(2-氨基苯甲酰基)丙酸; DL-犬尿氨酸

Database IDs

• CAS Number: 2126-91-2; 2922-83-0; 343-65-7
• EC Number: 206-445-9
• MDL Number: MFCD00025194
• Beilstein Number: 2697333
• PubChem SID: 162088142; 24882101
• PubChem CID: 846
• CHEBI ID: 57959
• CHEMBL: 498416
• Chemspider ID: 141580
• DrugBank ID: DB02070
• MeSH Name: Kynurenine
• Wikipedia Title: Kynurenine

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

PROPERTIES

Physical Property

• Solubility: Hot Water
• Apperance: Pale Yellow Solid
• Melting Point: ~235 °C (dec.); >190°C (dec.)

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0% (NT)
• Empirical Formula (Hill Notation): C10H12N2O3

DETAILS

MP Biomedicals - 05214103

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102125

Free Base
Light yellow crystals

Sigma Aldrich - 61250

Packaging
1 g in glass bottle
250 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 61250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - K661000

A 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

• 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)
• Mitsuhashi, S., et al.: Anal. Chim. Acta, 584, 315 (1990)