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Record Information
Version3.6
Creation Date2006-08-13 13:57:36 UTC
Update Date2017-03-02 21:27:30 UTC
HMDB IDHMDB04194
Secondary Accession NumbersNone
Metabolite Identification
Common NameN1-Methyl-4-pyridone-3-carboxamide
DescriptionN1-Methyl-4-pyridone-5-carboxamide (4PY ) is a normal human metabolite (one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation). 4PY concentration in serum is elevated in non-dialyzed chronic renal failure (CRF) patients when compared with controls. (PMID 12694300 ).
Structure
Thumb
Synonyms
ValueSource
1,4-dihydro-1-Methyl-4-oxo-3-pyridinecarboxamideChEBI
1-Methyl-4-oxo-1,4-dihydro-3-pyridinecarboxamideChEBI
1-Methyl-4-pyridone-3-carboximideChEBI
1-Methyl-4-pyridone-5-carboxamideChEBI
3-(Aminocarbonyl)-1-methyl-4(1H)-pyridoneChEBI
5-Aminocarbonyl-1-methyl-4(1H)-pyridoneChEBI
N'-methyl-4-pyridone-5-carboxamideChEBI
N-Methyl-4-pyridone-5-carboxamideChEBI
N1-Methyl-4-pyridone-5-carboxamideChEBI
1-Methyl-4-pyridone-3-carboxamideHMDB
Chemical FormulaC7H8N2O2
Average Molecular Weight152.1506
Monoisotopic Molecular Weight152.05857751
IUPAC Name1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide
Traditional Name1-methyl-4-oxopyridine-3-carboxamide
CAS Registry Number769-49-3
SMILES
CN1C=CC(=O)C(=C1)C(N)=O
InChI Identifier
InChI=1S/C7H8N2O2/c1-9-3-2-6(10)5(4-9)7(8)11/h2-4H,1H3,(H2,8,11)
InChI KeyKTLRWTOPTKGYQY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Nicotinamide
  • Dihydropyridine
  • Hydropyridine
  • Vinylogous amide
  • Heteroaromatic compound
  • Carboxamide group
  • Primary carboxylic acid amide
  • Cyclic ketone
  • Carboxylic acid derivative
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility115.0 mg/mLALOGPS
logP-1ALOGPS
logP-0.56ChemAxon
logS-0.12ALOGPS
pKa (Strongest Acidic)15.73ChemAxon
pKa (Strongest Basic)0.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.4 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.81 m3·mol-1ChemAxon
Polarizability14.7 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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 Quantified0.26 +/- 0.09 uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified2.8 (1.4-7.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified4.19 +/- 3.10 uMAdult (>18 years old)Bothuremia details
    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 IDFDB023331
    KNApSAcK IDNot Available
    Chemspider ID389671
    KEGG Compound IDC05843
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB04194
    Metagene LinkHMDB04194
    METLIN IDNot Available
    PubChem Compound440810
    PDB IDNot Available
    ChEBI ID27838
    References
    Synthesis ReferenceChaykin, Sterling. Biosynthesis of N-methyl-4-pyridone-3-carboxamide. Biochimica et Biophysica Acta, General Subjects (1964), 82(3), 633-4.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. 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. [PubMed: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-4-pyridone-3-carboxamide + Hydrogen peroxide + Hydrogen Iondetails