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

• ChemBase ID: 1833
• Molecular Formular: C10H12N2O3
• Molecular Mass: 208.21388
• Monoisotopic Mass: 208.08479225
• SMILES: N[C@@H](CC(=O)c1ccccc1N)C(=O)O
• Canonical SMILES: OC(=O)[C@H](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)/t8-/m0/s1
• InChIKey: YGPSJZOEDVAXAB-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
• IUPAC Traditional name: L-kynurenine
• Synonyms: L-2-Amino-4-[2-Aminophenyl]-4-Oxobutanoic Acid; β-Anthraniloyl-L-alanine; L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid; L-Kynurenine

Database IDs

• CAS Number: 2922-83-0
• MDL Number: MFCD00069912
• PubChem SID: 46507622; 160965288; 24896246
• PubChem CID: 161166

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -1.93
• LOG S: -2.1
• Solubility (Water): 1.67e+00 g/l

PROPERTIES

Physical Property

• Apperance: light yellow crystalline

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C10H12N2O3

DETAILS

DrugBank - DB02070

Drug information: experimental

Sigma Aldrich - K8625

Biochem/physiol Actions
Key intermediate in the breakdown pathway of tryptophan.
L-Kynurenine is a key intermediate in the breakdown of L-tryptophan and the formation of nicotinamide adenine dinucleotide (NAD+) via the kynurenine pathway. L-kynurenine is involved in a variety of neurological processes and diseases. L-kynurenine is a substrate for kynureninase/kynurenine hydrolase; kynurenine 3-monooxygenase and kynurenine-oxoglutarate transaminase.