2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxo(1,2-13C2)butanoic acid

• ChemBase ID: 170689
• Molecular Formular: C10H12N2O4
• Molecular Mass: 227.19199857
• Monoisotopic Mass: 227.08345144
• SMILES: c1(cccc(c1N)C(=O)C[13CH]([13C](=O)O)[15NH2])O
• Canonical SMILES: O[13C](=O)[13CH](CC(=O)c1cccc(c1N)O)[15NH2]
• InChI: InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)/i6+1,10+1,11+1
• InChIKey: VCKPUUFAIGNJHC-BTOQUXKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxo(1,2-^1^3C₂)butanoic acid
• IUPAC Traditional name: 2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxo(1,2-^1^3C₂)butanoic acid
• Synonyms: α,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic Acid-13C2,15N; 3-(3-Hydroxyanthraniloyl)alanine-13C2,15N; 3-Hydroxy-DL-kynurenine-13C2,15N; 3-Hydroxykynurenine-13C2,15N; DL-3-Hydroxykynurenine; Hydroxykynurenine-13C2,15N; NSC 96400-13C2,15N; rac 3-Hydroxy Kynurenine-13C2,15N

Database IDs

• PubChem SID: 164226599
• PubChem CID: 71749085

CALCULATED PROPERTIES

• Acid pKa: 0.9866217
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.2143626
• LogD (pH = 7.4): -2.2238457
• Log P: -2.2125268
• Molar Refractivity: 57.0311 cm^3
• Polarizability: 21.611448 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943697

Labelled analogue of 3-Hydroxykynurenine is a metabolite of tryptophan. 3-Hydroxykynurenine filters UV light in the human lens. Studies suggest that Hydroxykynurenine is an endogenous oxidative stress generator and a potential endogenous neurotoxin.

REFERENCES

• Malina, H.Z. et al.: Graefes. Arch. Clin. Exp. Ophthalmol., 233, 38 (1995)
• Okuda, S. et al.: J. Neurochem., 70, 299 (1995)