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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 16:09:03 UTC
Update Date2021-09-14 15:46:17 UTC
HMDB IDHMDB0240342
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetylkynurenine
DescriptionN-Acetylkynurenine (CAS: 2044-53-3) 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. N-Acetylkynurenine has been identified in urine (PMID: 6051633 ).
Structure
Data?1591301930
Synonyms
ValueSource
AcetylkynurenineHMDB
Nalpha-acetyl-L-kynurenineHMDB
Nalpha-acetylkynurenineHMDB
Nα-acetyl-L-kynurenineHMDB
Nα-acetylkynurenineHMDB
alpha-(Acetylamino)-2-amino-gamma-oxobenzenebutanoic acidHMDB
Α-(acetylamino)-2-amino-γ-oxobenzenebutanoic acidHMDB
N-AcetylkynurenineHMDB
Chemical FormulaC12H14N2O4
Average Molecular Weight250.254
Monoisotopic Molecular Weight250.095356939
IUPAC Name(2S)-4-(2-aminophenyl)-2-acetamido-4-oxobutanoic acid
Traditional Name(2S)-4-(2-aminophenyl)-2-acetamido-4-oxobutanoic acid
CAS Registry Number3428-08-8
SMILES
CC(=O)N[C@@H](CC(=O)C1=C(N)C=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C12H14N2O4/c1-7(15)14-10(12(17)18)6-11(16)8-4-2-3-5-9(8)13/h2-5,10H,6,13H2,1H3,(H,14,15)(H,17,18)/t10-/m0/s1
InChI KeyPPIMFXHQDQRWGJ-JTQLQIEISA-N
Chemical Taxonomy
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
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Butyrophenone
  • Alpha-amino acid or derivatives
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Gamma-keto acid
  • Benzoyl
  • Benzenoid
  • Keto acid
  • Monocyclic benzene moiety
  • Acetamide
  • Vinylogous amide
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Indirect biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(0.4) g/LALOGPS
logP10(-0.057) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)2.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.49 m³·mol⁻¹ChemAxon
Polarizability24.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylkynurenine,1TMS,#1CC(=O)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C2310.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
N-Acetylkynurenine,1TMS,#2CC(=O)N[C@@H](CC(=O)C1=CC=CC=C1N[Si](C)(C)C)C(=O)O2395.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
N-Acetylkynurenine,1TMS,#3CC(=O)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C2278.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
N-Acetylkynurenine,1TBDMS,#1CC(=O)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C2564.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
N-Acetylkynurenine,1TBDMS,#2CC(=O)N[C@@H](CC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C)C(=O)O2644.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
N-Acetylkynurenine,1TBDMS,#3CC(=O)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C2518.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylkynurenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylkynurenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylkynurenine 10V, Positive-QTOFsplash10-0a4i-0790000000-5cd7f19441ce4db136702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylkynurenine 20V, Positive-QTOFsplash10-03kc-0900000000-bcb7c751bc7ebac128212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylkynurenine 40V, Positive-QTOFsplash10-0006-9500000000-726c1efb9f3e9eec99332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylkynurenine 10V, Negative-QTOFsplash10-0006-0920000000-d8696988fa88485412cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylkynurenine 20V, Negative-QTOFsplash10-052u-9600000000-7a020fc740a34065dbb02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylkynurenine 40V, Negative-QTOFsplash10-0006-9200000000-e88f3520cac33b2b85b42021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54201144
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Benassi CA, Veronese FM, De Antoni A: On the determination of small amounts of tryptophan metabolites and their occurrence in normal human urine. Clin Chim Acta. 1967 Sep;17(3):383-91. doi: 10.1016/0009-8981(67)90213-6. [PubMed:6051633 ]
  2. Mair RD, Sirich TL, Plummer NS, Meyer TW: Characteristics of Colon-Derived Uremic Solutes. Clin J Am Soc Nephrol. 2018 Sep 7;13(9):1398-1404. doi: 10.2215/CJN.03150318. Epub 2018 Aug 7. [PubMed:30087103 ]