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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:49:09 UTC
HMDB IDHMDB0000732
Secondary Accession Numbers
  • HMDB00732
  • HMDB01152
Metabolite Identification
Common NameHydroxykynurenine
DescriptionHydroxykynurenine is a free radical generator and a bioprecursor quinolinic acid which is a endogenous excitotoxin (PMID 16697652 ). It is a product of enzyme kynurenine 3-monooxygenase in the tryptophan catabolism pathway (Reactome http://www.reactome.org).
Structure
Thumb
Synonyms
ValueSource
2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoic acidChEBI
3-(3-Hydroxyanthraniloyl)alanineChEBI
3-Hydroxy-DL-kynurenineChEBI
2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoateGenerator
3-(3-Hydroxyanthraniloyl)-alanineHMDB
3-Hydroxy-kynurenineHMDB
3-HydroxykynurenineHMDB
DL-3-HydroxykynurenineHMDB
HydroxykinurenineHMDB
OH-KynurenineHMDB
3-Hydroxykynurenine, (DL)-isomerMeSH
3-Hydroxykynurenine, (D)-isomerMeSH
3-Hydroxykynurenine, (L)-isomerMeSH
Chemical FormulaC10H12N2O4
Average Molecular Weight224.2133
Monoisotopic Molecular Weight224.079706882
IUPAC Name2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Traditional Namehydroxykynurenine
CAS Registry Number484-78-6
SMILES
NC(CC(=O)C1=C(N)C(O)=CC=C1)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)
InChI KeyVCKPUUFAIGNJHC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Benzoyl
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • Aminophenol
  • Gamma-keto acid
  • O-aminophenol
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Keto acid
  • Benzenoid
  • Beta-aminoketone
  • Monocyclic benzene moiety
  • Primary aromatic amine
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point217 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.33 g/LALOGPS
logP-2.1ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m³·mol⁻¹ChemAxon
Polarizability21.79 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0159-0692000000-b9c2999ae2687722738cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0159-0692000000-b9c2999ae2687722738cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0690000000-2458bca60bd4d63d4e0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-2900000000-9f7c3e5d9fdd069332efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05y3-9600000000-0a276981035bdfdaa384View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a7l-0980000000-d29afe0493d7b1747eceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0c0r-0910000000-05ae10fbc19a32189675View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03k9-1900000000-0a8a8247ae2ccdceccc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-6900000000-d831db1fd30714ed7af0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004j-9400000000-b9afef7c45866b074926View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0190000000-ff6859f21558ded760b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03xr-0900000000-96098b3be4cea5d8ba14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-006x-0900000000-6393e30c9fa764800712View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0ik9-0900000000-4f9bd3b6476d74c41a74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-972b9ebadf10c99787c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01qa-0900000000-301763df64398d3bd889View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0090000000-81fc171e92a48af06573View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0a6r-0190000000-408a1da9eaf96a6aa006View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0910000000-d216d77a1ba053893773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0910000000-d216d77a1ba053893773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0920000000-385b607aaff360ab6caaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Brain
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.05 (0.00-0.10) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.77 (0.46-5.13) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.15 (0.06-0.34) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022210
KNApSAcK IDNot Available
Chemspider ID87
KEGG Compound IDC02794
BioCyc ID3-HYDROXY-L-KYNURENINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5700
PubChem Compound89
PDB IDNot Available
ChEBI ID1547
References
Synthesis ReferenceKotake, Munio; Sakan, Takeo; Senoh, Shiro. Amino acids. IV. The synthesis of 3-hydroxykynurenine. J. Inst. Polytech., Osaka. City Univ. (1950), 1(No. 2), 35-41. CAN 46:2639 AN 1952:2639
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Schwarcz R, Rassoulpour A, Wu HQ, Medoff D, Tamminga CA, Roberts RC: Increased cortical kynurenate content in schizophrenia. Biol Psychiatry. 2001 Oct 1;50(7):521-30. [PubMed:11600105 ]
  3. Pearson SJ, Reynolds GP: Determination of 3-hydroxykynurenine in human brain and plasma by high-performance liquid chromatography with electrochemical detection. Increased concentrations in hepatic encephalopathy. J Chromatogr. 1991 Apr 19;565(1-2):436-40. [PubMed:1874889 ]
  4. Reynolds GP, Pearson SJ: Neurochemical-clinical correlates in Huntington's disease--applications of brain banking techniques. J Neural Transm Suppl. 1993;39:207-14. [PubMed:8103075 ]
  5. Reynolds GP, Pearson SJ: Increased brain 3-hydroxykynurenine in Huntington's disease. Lancet. 1989 Oct 21;2(8669):979-80. [PubMed:2571888 ]
  6. Guidetti P, Reddy PH, Tagle DA, Schwarcz R: Early kynurenergic impairment in Huntington's disease and in a transgenic animal model. Neurosci Lett. 2000 Apr 14;283(3):233-5. [PubMed:10754231 ]
  7. Pearson SJ, Reynolds GP: Increased brain concentrations of a neurotoxin, 3-hydroxykynurenine, in Huntington's disease. Neurosci Lett. 1992 Sep 14;144(1-2):199-201. [PubMed:1436703 ]
  8. Lee HJ, Bach JH, Chae HS, Lee SH, Joo WS, Choi SH, Kim KY, Lee WB, Kim SS: Mitogen-activated protein kinase/extracellular signal-regulated kinase attenuates 3-hydroxykynurenine-induced neuronal cell death. J Neurochem. 2004 Feb;88(3):647-56. [PubMed:14720214 ]
  9. Guidetti P, Bates GP, Graham RK, Hayden MR, Leavitt BR, MacDonald ME, Slow EJ, Wheeler VC, Woodman B, Schwarcz R: Elevated brain 3-hydroxykynurenine and quinolinate levels in Huntington disease mice. Neurobiol Dis. 2006 Jul;23(1):190-7. Epub 2006 May 12. [PubMed:16697652 ]

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the hydroxylation of L-kynurenine (L-Kyn) to form 3-hydroxy-L-kynurenine (L-3OHKyn). Required for synthesis of quinolinic acid, a neurotoxic NMDA receptor antagonist and potential endogenous inhibitor of NMDA receptor signaling in axonal targeting, synaptogenesis and apoptosis during brain development. Quinolinic acid may also affect NMDA receptor signaling in pancreatic beta cells, osteoblasts, myocardial cells, and the gastrointestinal tract.
Gene Name:
KMO
Uniprot ID:
O15229
Molecular weight:
55809.445
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5