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Record Information
Version3.6
Creation Date2006-08-13 13:56:50 UTC
Update Date2016-02-11 01:06:37 UTC
HMDB IDHMDB04193
Secondary Accession NumbersNone
Metabolite Identification
Common NameN1-Methyl-2-pyridone-5-carboxamide
DescriptionN-methyl-2-pyridone-5-carboxamide (2PY) is one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation. Increased serum 2PY concentrations are observed in chronic renal failure (CRF) patients, which along with the deterioration of kidney function and its toxic properties (significant inhibition of PARP-1), suggests that 2PY is an uremic toxin. (PMID 12694300 ).
Structure
Thumb
Synonyms
ValueSource
1-Methyl-5-carboxylamide-2-pyridoneChEBI
N'-methyl-2-pyridone-5-carboxamideChEBI
N(1)-Methyl-2-pyridone-5-carboxamideChEBI
N-Methyl-2-pyridone-5-carboxamideChEBI
N'Methyl-2-pyridone-5-carboxamideHMDB
Chemical FormulaC7H8N2O2
Average Molecular Weight152.1506
Monoisotopic Molecular Weight152.05857751
IUPAC Name1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide
Traditional Name1-methyl-6-oxopyridine-3-carboxamide
CAS Registry Number701-44-0
SMILES
CN1C=C(C=CC1=O)C(N)=O
InChI Identifier
InChI=1S/C7H8N2O2/c1-9-4-5(7(8)11)2-3-6(9)10/h2-4H,1H3,(H2,8,11)
InChI KeyInChIKey=JLQSXXWTCJPCBC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Nicotinamide
  • Pyridinone
  • Dihydropyridine
  • Hydropyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility41.4 mg/mLALOGPS
logP-0.96ALOGPS
logP-1.1ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)15.93ChemAxon
pKa (Strongest Basic)1.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.4 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.76 m3·mol-1ChemAxon
Polarizability14.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-b64dc5db3a8f82da3c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1900000000-7da53351adedc1e67e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zir-9300000000-28053d0ec9ded55ae3cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-e93df4f3c2c8f4de0322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2900000000-36e016881280d17eaae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-282653b830a8366d9872View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048map00760
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.00 +/- 4.47 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.3 (5.7-10.2) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.71 (0.13-2.88) umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified2.0 (0.67-5.10) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified5.75 (1.92-12.63) umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified4.8 (1.86-13.94) umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified5.6 (4.6-6.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified51.27 +/- 23.66 uMAdult (>18 years old)Bothuremia details
UrineDetected and Quantified41.00 (16.00-66.00) umol/mmol creatinineAdult (>18 years old)BothPellagra details
Associated Disorders and Diseases
Disease References
Pellagra
  1. Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [17709435 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023330
KNApSAcK IDNot Available
Chemspider ID62899
KEGG Compound IDC05842
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04193
Metagene LinkHMDB04193
METLIN ID7025
PubChem Compound69698
PDB IDNot Available
ChEBI ID27410
References
Synthesis ReferenceGrudzinski, Stefan. Preparation of N-methyl-2-pyridone-5-carboxamide. Roczniki Chemii (1962), 36 1705-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Carter EG: Quantitation of urinary niacin metabolites by reversed-phase liquid chromatography. Am J Clin Nutr. 1982 Nov;36(5):926-30. [6215856 ]
  2. Patterson JI, Brown RR, Linkswiler H, Harper AE: Excretion of tryptophan-niacin metabolites by young men: effects of tryptophan, leucine, and vitamin B6 intakes. Am J Clin Nutr. 1980 Oct;33(10):2157-67. [6448542 ]
  3. Rutkowski B, Slominska E, Szolkiewicz M, Smolenski RT, Striley C, Rutkowski P, Swierczynski J: N-methyl-2-pyridone-5-carboxamide: a novel uremic toxin? Kidney Int Suppl. 2003 May;(84):S19-21. [12694300 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
1-Methylnicotinamide + Oxygen + Water → N1-Methyl-2-pyridone-5-carboxamide + Hydrogen peroxide + Hydrogen Iondetails