2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid

• ChemBase ID: 102525
• Molecular Formular: C10H12N2O4
• Molecular Mass: 224.21328
• Monoisotopic Mass: 224.07970687
• SMILES: NC(CC(=O)c1cccc(O)c1N)C(=O)O
• Canonical SMILES: OC(=O)C(CC(=O)c1cccc(c1N)O)N
• 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)
• InChIKey: VCKPUUFAIGNJHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
• IUPAC Traditional name: 3-hydroxy-DL-kynurenine; hydroxykynurenine
• Synonyms: α,2-Diamino-3-hydroxy-β-oxobenzenebutanoic acid; 3-HYDROXY-DL-KYNURENINE; 3-Hydroxykynurenine; α,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic acid; 3-Hydroxy-DL-kynurenine; 3-(3-Hydroxyanthraniloyl)alanine; 3-Hydroxy-DL-kynurenine; 3-Hydroxykynurenine; DL-3-Hydroxykynurenine; Hydroxykynurenine; NSC 96400; rac 3-Hydroxy Kynurenine

Database IDs

• CAS Number: 484-78-6; 2147-61-7
• MDL Number: MFCD00047832
• PubChem SID: 24895482; 162089922
• PubChem CID: 89
• CHEBI ID: 1547
• CHEMBL: 442576
• Chemspider ID: 87
• KEGG ID: C02794
• MeSH Name: 3-hydroxykynurenine
• Wikipedia Title: 3-Hydroxykynurenine

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

PROPERTIES

Safety Information

• Storage Condition: 2-8°C, Desiccate, Protect from light
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C10H12N2O4

DETAILS

MP Biomedicals - 02102003

Monamine Oxidase Substrate
Crystalline

Sigma Aldrich - H1771

Biochem/physiol Actions
A tryptophan metabolite; a chromophore present in the lens of the eye.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1771.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1771.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H943695

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)