CAS 2147-61-7|CAS 484-78-6|3-hydroxy-DL-kynurenine|2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid|α,2-Diamino-3-hydroxy-β-oxobenzenebutanoic acid|3-HYDROXY-DL-KYNURENINE|hydroxyky...

General Information

Structure

Molecular Formula

C₁₀H₁₂N₂O₄

Molecular Mass

224.21328

Exact Mass

224.07970687

Charge

0

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

Canonic Smiles

OC(=O)C(CC(=O)c1cccc(c1N)O)N

Isomeric Smiles

NC(CC(=O)c1cccc(O)c1N)C(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-2.22

LogD (pH = 5.5)

-2.21

Log P

-2.21

Rotatable Bonds

4

H Donor

4

H Acceptors

6

Lipinski's Rule of Five

true

Acid pKa

0.99

Polar Surface Area

126.64

Polarizability

21.75

Molar Refractivity

57.03

LOG S

-1.34

Data Source

Commercial Catalog

Academic Data

89

Data Source

Names and Identifiers

IUPAC Traditional name

3-hydroxy-DL-kynurenine hydroxykynurenine

IUPAC name

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

Synonyms

α,2-Diamino-3-hydroxy-β-oxobenzenebutanoic acid3-HYDROXY-DL-KYNURENINE3-Hydroxykynurenine3-Hydroxy-DL-kynurenineα,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic acidrac 3-Hydroxy KynurenineHydroxykynurenineNSC 96400DL-3-Hydroxykynurenine3-(3-Hydroxyanthraniloyl)alanine3-Hydroxykynurenine3-Hydroxy-DL-kynurenine3-hydroxykynurenine2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid3-Hydroxy-DL-kynurenine3-(3-hydroxyanthraniloyl)alanine3-Hydroxykynurenine

Names and Identifiers

Registration numbers

CAS Number

2147-61-7484-78-6

PubChem CID

89

PubChem SID

1620899222489548214717840

KEGG ID

Chemspider ID

Wikipedia Title

CHEMBL

CHEBI ID

MeSH Name

MDL Number

UniProt Database

Q16719Q64240P01876Q62577P20758Q07456P02760Q60559P36992P00978P04366

Reaxys Registry

2697635

Patent number

US2007184114US2008076796

ACToR Database

2147-61-7606-14-4

MetaboLights Database

MTBLS2295MTBLS697MTBLS1040MTBLS362MTBLS3628MTBLS816MTBLS2483MTBLS444MTBLS205MTBLS1906MTBLS2878MTBLS1861MTBLS1221MTBLS1115MTBLS787MTBLS3852MTBLS4722

SABIO-RK Database

12047256420071395114357120451203812046

PubMed Citation Links

1520672611477208

SureChEMBL Database

SCHEMBL180582

BRENDA Database

3.7.1.34.1.1.282.6.1.73.5.1.9

HMDB Database

HMDB0000732

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C10H12N2O4

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02102003

Monamine Oxidase Substrate
Crystalline

Wikipedia

3-Hydroxykynurenine

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.

TRC

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.

ChEBI

CHEBI:1547

A hydroxykynurenine that is kynurenine substituted by a hydroxy group at position 3.

Molecule Details

References

PubChem Literature

From Data Sources

• Okuda, S. et al.: J. Neurochem., 70, 299 (1995)

• Malina, H.Z. et al.: Graefes. Arch. Clin. Exp. Ophthalmol., 233, 38 (1995)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:102525