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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 13:57:36 UTC
Update Date2020-02-26 21:25:02 UTC
HMDB IDHMDB0004194
Secondary Accession Numbers
  • HMDB04194
Metabolite Identification
Common NameN1-Methyl-4-pyridone-3-carboxamide
DescriptionN1-Methyl-4-pyridone-3-carboxamide, also known as 5-aminocarbonyl-1-methyl-4(1H)-pyridone, 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. N1-Methyl-4-pyridone-3-carboxamide is an extremely weak basic (essentially neutral) compound (based on its pKa). N1-methyl-4-pyridone-3-carboxamide can be biosynthesized from 1-methylnicotinamide; which is catalyzed by the enzyme aldehyde oxidase. In humans, N1-methyl-4-pyridone-3-carboxamide is involved in nicotinate and nicotinamide metabolism. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. N1-Methyl-4-pyridone-3-carboxamide is a potentially toxic compound. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. Increased levels of uremic toxins can stimulate the production of reactive oxygen species. 4PY concentration in serum is elevated in non-dialyzed chronic renal failure (CRF) patients when compared with controls. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Structure
Data?1582752302
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
Description 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
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.81 m³·mol⁻¹ChemAxon
Polarizability14.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-4900000000-20331ed897c9e0a9fc31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-584bee8b1d116d28ad72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2i-0900000000-9b1ca159ad8a687a6449Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9500000000-8c23a4085269713574deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-fdc0b46552431f575ba6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2900000000-280bfbe85df4a0da0894Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-9200000000-ca4c67126b692467c9eeSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified4.19 +/- 3.10 uMAdult (>18 years old)Bothuremia details
    Associated Disorders and Diseases
    Disease References
    Uremia
    1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB023331
    KNApSAcK IDNot Available
    Chemspider ID389671
    KEGG Compound IDC05843
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound440810
    PDB IDNot Available
    ChEBI ID27838
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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 ]
    2. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

    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