Record Information
Version1.0
Creation date2011-09-21 00:09:43 UTC
Update date2019-11-26 03:21:01 UTC
Primary IDFDB022181
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Kynurenine
DescriptionKynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-kynurenine is a central compound of the pathway of tryptophan metabolism pathway since it can change to the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders. It can occur in neurodegenerative disorders, such as Parkinson's disease, Huntington's and Alzheimer's disease, in stroke, in epilepsy, in multiple sclerosis, in amyotrophic lateral sclerosis, and in mental failures, such as schizophrenia and depression. [HMDB]
CAS Number2922-83-0
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acidChEBI
3-Anthraniloyl-L-alanineChEBI
KYNURENINEChEBI
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoateGenerator
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
3-Anthraniloyl-alanineHMDB
3-AnthraniloylalanineHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoateHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoic acidHMDB
DL-KynurenineHMDB
KynureninHMDB
QuinurenineHMDB
L-KynurenineHMDB
3-(2-aminobenzoyl)-L-alanineHMDB
KYNAHMDB
(2S)-2-amino-4-(2-Aminophenyl)-4-oxobutanoateGenerator
(2S)-2-amino-4-(2-Aminophenyl)-4-oxobutanoic acidChEBI
(alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoatehmdb
(alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acidhmdb
(S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoatehmdb
(S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acidhmdb
3-(3-Hydroxyanthraniloyl)-L-alanineHMDB
3-anthraniloyl-Alaninehmdb
3-anthraniloyl-L-alaninehmdb
3-Hydroxy-L-kynurenineHMDB
alpha,2-diamino-gamma-oxo-Benzenebutanoatehmdb
alpha,2-diamino-gamma-oxo-Benzenebutanoic acidhmdb
dl-Kynureninehmdb
DL-Kynureninefree basehmdb
Predicted Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12N2O3
IUPAC name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
InChI IdentifierInChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
InChI KeyYGPSJZOEDVAXAB-QMMMGPOBSA-N
Isomeric SMILESN[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
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
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Benzoyl
  • Gamma-keto acid
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Benzenoid
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-014l-0931000000-29fa7c323b035cb399d3Spectrum
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-014l-0931000000-29fa7c323b035cb399d3Spectrum
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-014l-0931000000-a43ae0acafac266101c4Spectrum
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-0006-1910000000-fdc25d09b4da4b1d7657Spectrum
Predicted GC-MSL-Kynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9500000000-d7bf6a26c74e0dcabf40Spectrum
Predicted GC-MSL-Kynurenine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4920000000-cb575b96b16b3ef9130fSpectrum
Predicted GC-MSL-Kynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Kynurenine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Kynurenine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Kynurenine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Kynurenine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Kynurenine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-2910000000-366ce08b5736d68dfad02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01bd-5900000000-c18e10be7e029474cf032012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9300000000-0f8238d38819f6f30d122012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0790000000-3fa45266412288bf1c622012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0007-3900000000-a66f45aff81960af75752012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xv-5900000000-15442ec5aaef005401ae2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r7-7900000000-0833fe9d2739d329f1972012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-d5d45364462a730de4362012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0900000000-13929f0bde71b6326d3f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0f6w-2900000000-b2d4f361ffee9fd93bb72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004j-0900000000-96930a886f7bbcc44df32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-2441a358973abdb063da2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-dc4fee4751d6295751572012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-4ec06cc06a3eab2625d62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-319acefac99779fa75522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-4280b92b875a6f754a912017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-664e2c8904363418682e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-aa6188977ba2f460f5bc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-ee71a364df13bd095feb2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r7-0920000000-f2e6efdd3988d3010e332016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022a-3900000000-e1c06099462847ad5b972016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9700000000-a9df2d5ca325f97f69f12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2490000000-9604ae0cc9d437acd8782016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9520000000-8f0ea7d174290496860d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-9721076505654380d2de2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID141580
ChEMBL IDCHEMBL498416
KEGG Compound IDC00328
Pubchem Compound ID161166
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02070
HMDB IDHMDB00684
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1445574
KNApSAcK IDNot Available
HET IDKYN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDKynurenine
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
Aspartate aminotransferase, mitochondrialGOT2P00505
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