Record Information
Version1.0
Creation date2011-09-21 01:38:04 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028330
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-3-Hydroxykynurenine
DescriptionL-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). 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) [HMDB]
CAS Number606-14-4
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acidChEBI
3-(3-Hydroxyanthraniloyl)-L-alanineChEBI
(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoateGenerator
3-(2-Amino-3-hydroxybenzoyl)-L-alanineHMDB
3-Hydroxy-L-kynurenineHMDB
L-3-HKHMDB
(2S)-2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoateGenerator
(2S)-2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoic acidChEBI
3-(2-amino-3-hydroxybenzoyl)-L-alaninehmdb
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
Polarizability21.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12N2O4
IUPAC name(2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
InChI IdentifierInChI=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 KeyVCKPUUFAIGNJHC-LURJTMIESA-N
Isomeric SMILESN[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O
Average Molecular Weight224.2133
Monoisotopic Molecular Weight224.079706882
Classification
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • L-alpha-amino acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • O-aminophenol
  • Gamma-keto acid
  • Aminophenol
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Keto acid
  • Beta-aminoketone
  • Benzenoid
  • Monocyclic benzene moiety
  • 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:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-3-Hydroxykynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-057u-7910000000-88ad37433d9fe2009b5eSpectrum
Predicted GC-MSL-3-Hydroxykynurenine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-8379000000-0b0a9595aae2502a55acSpectrum
Predicted GC-MSL-3-Hydroxykynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0960000000-c33d63911a63b0e550592016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0209-2900000000-733debea97f59a15a6202016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-6900000000-908957a56bc62255065a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1290000000-49db02e2f97330c6041f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9650000000-45bd0384724255104d6c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-7900000000-e62c0de8b7c63b9e40662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0890000000-24d8093dfa7cd74719592021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-070i-1900000000-3159845d0fd09fc5476c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9700000000-c823da7e7ec85255fba02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0690000000-e55cff3d90188bbe1b4f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-15ef15dcef2ce9fdfef52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-2b99b24490fd7fc7a3f92021-09-24View Spectrum
NMRNot Available
ChemSpider ID11318
ChEMBL IDNot Available
KEGG Compound IDC03227
Pubchem Compound ID11811
Pubchem Substance IDNot Available
ChEBI ID17380
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11631
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference