Human Metabolome Database Version 3.5

Showing metabocard for L-3-Hydroxykynurenine (HMDB11631)

Record Information
Version 3.5
Creation Date 2009-01-30 07:47:12 -0700
Update Date 2013-05-29 13:46:32 -0600
HMDB ID HMDB11631
Secondary Accession Numbers None
Metabolite Identification
Common Name L-3-Hydroxykynurenine
Description L-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088 Link_out). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-(2-Amino-3-hydroxybenzoyl)-L-alanine
  2. 3-(3-Hydroxyanthraniloyl)-L-alanine
  3. 3-Hydroxy-L-kynurenine
  4. L-3-HK
Chemical Formula C10H12N2O4
Average Molecular Weight 224.2133
Monoisotopic Molecular Weight 224.079706882
IUPAC Name (2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Traditional IUPAC Name 3-hydroxy-L-kynurenine
CAS Registry Number 606-14-4
SMILES N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O
InChI Identifier 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)/t6-/m0/s1
InChI Key VCKPUUFAIGNJHC-LURJTMIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • amino acid zwitterion(ChEBI)
Substituents
  • Acetophenone
  • Aminobenzoate
  • Aminophenol Derivative
  • Aniline
  • Benzoyl
  • Beta Aminoketone
  • Carboxylic Acid
  • Gamma Keto Acid
  • Ketone
  • Phenol
  • Phenol Derivative
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.33 g/L ALOGPS
LogP -2.09 ALOGPS
LogP -2.2 ChemAxon
LogS -1.83 ALOGPS
pKa (strongest acidic) 0.99 ChemAxon
pKa (strongest basic) 8.9 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 126.64 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 57.03 ChemAxon
Polarizability 21.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 map00380 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected and Quantified
2.2 (1.0-3.4) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028330
KNApSAcK ID Not Available
Chemspider ID 11318 Link_out
KEGG Compound ID C03227 Link_out
BioCyc ID 3-HYDROXY-L-KYNURENINE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11631 Link_out
Metagene Link HMDB11631 Link_out
METLIN ID Not Available
PubChem Compound 11811 Link_out
PDB ID Not Available
ChEBI ID 17380 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Sardar AM, Bell JE, Reynolds GP: Increased concentrations of the neurotoxin 3-hydroxykynurenine in the frontal cortex of HIV-1-positive patients. J Neurochem. 1995 Feb;64(2):932-5. Pubmed: 7830088 Link_out
  2. Guidetti P, Schwarcz R: 3-Hydroxykynurenine potentiates quinolinate but not NMDA toxicity in the rat striatum. Eur J Neurosci. 1999 Nov;11(11):3857-63. Pubmed: 10583474 Link_out

Enzymes
Name: Kynureninase
Reactions:
L-3-Hydroxykynurenine + Water unknown 3-Hydroxyanthranilic acid + L-Alanine details
Gene Name: KYNU
Uniprot ID: Q16719 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial
Reactions:
L-3-Hydroxykynurenine + Oxoglutaric acid unknown 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic acid details
Gene Name: AADAT
Uniprot ID: Q8N5Z0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Kynurenine--oxoglutarate transaminase 1
Reactions:
L-3-Hydroxykynurenine + Oxoglutaric acid unknown 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic acid details
Gene Name: CCBL1
Uniprot ID: Q16773 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Kynurenine 3-monooxygenase
Reactions:
L-Kynurenine + NADPH + Oxygen unknown L-3-Hydroxykynurenine + NADP + Water details
L-Kynurenine + Oxygen + NADPH + Hydrogen Ion unknown L-3-Hydroxykynurenine + NADP + Water details
Gene Name: KMO
Uniprot ID: O15229 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Kynurenine--oxoglutarate transaminase 3
Reactions:
L-3-Hydroxykynurenine + Oxoglutaric acid unknown 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic acid details
Gene Name: CCBL2
Uniprot ID: Q6YP21 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA