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Record Information
Version5.0
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. NN1-Methyl-4-pyridone-3-carboxamide (4PY ) is a normal human metabolite (one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation). 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 mediated by the enzyme aldehyde oxidase. In humans, N1-methyl-4-pyridone-3-carboxamide is involved in nicotinate and nicotinamide metabolism. N1-Methyl-4-pyridone-3-carboxamide is a potentially toxic compound. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. As a uremic toxin, this compound can cause uremic syndrome.
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

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility115 g/LALOGPS
logP10(-1) g/LALOGPS
logP10(-0.56) g/LChemAxon
logS10(-0.12) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.05431661259
DarkChem[M-H]-130.21931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N1-Methyl-4-pyridone-3-carboxamideCN1C=CC(=O)C(=C1)C(N)=O1798.2Standard polar33892256
N1-Methyl-4-pyridone-3-carboxamideCN1C=CC(=O)C(=C1)C(N)=O1572.3Standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamideCN1C=CC(=O)C(=C1)C(N)=O2042.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N1-Methyl-4-pyridone-3-carboxamide,1TMS,isomer #1CN1C=CC(=O)C(C(=O)N[Si](C)(C)C)=C11665.2Semi standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,1TMS,isomer #1CN1C=CC(=O)C(C(=O)N[Si](C)(C)C)=C11815.1Standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,1TMS,isomer #1CN1C=CC(=O)C(C(=O)N[Si](C)(C)C)=C12070.1Standard polar33892256
N1-Methyl-4-pyridone-3-carboxamide,2TMS,isomer #1CN1C=CC(=O)C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C11716.2Semi standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,2TMS,isomer #1CN1C=CC(=O)C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C11847.3Standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,2TMS,isomer #1CN1C=CC(=O)C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C12009.1Standard polar33892256
N1-Methyl-4-pyridone-3-carboxamide,1TBDMS,isomer #1CN1C=CC(=O)C(C(=O)N[Si](C)(C)C(C)(C)C)=C11922.1Semi standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,1TBDMS,isomer #1CN1C=CC(=O)C(C(=O)N[Si](C)(C)C(C)(C)C)=C12013.0Standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,1TBDMS,isomer #1CN1C=CC(=O)C(C(=O)N[Si](C)(C)C(C)(C)C)=C12210.6Standard polar33892256
N1-Methyl-4-pyridone-3-carboxamide,2TBDMS,isomer #1CN1C=CC(=O)C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12202.4Semi standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,2TBDMS,isomer #1CN1C=CC(=O)C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12236.1Standard non polar33892256
N1-Methyl-4-pyridone-3-carboxamide,2TBDMS,isomer #1CN1C=CC(=O)C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12209.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-4900000000-20331ed897c9e0a9fc312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 30V, Positive-QTOFsplash10-0006-9200000000-1cb822771a6ad4a055752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 0V, Positive-QTOFsplash10-0udr-0900000000-1d0361e9faeabeb712622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Positive-QTOFsplash10-000i-0900000000-6f959701aa7326eb0c632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 0V, Positive-QTOFsplash10-0udr-0900000000-208827e4de225e9d8d632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Positive-QTOFsplash10-000i-0900000000-f55ef59743379eae48ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 30V, Positive-QTOFsplash10-0006-9200000000-ae1cfccb1887632aa1472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 20V, Positive-QTOFsplash10-000i-4900000000-63099c0a130f1a93fd192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Positive-QTOFsplash10-000i-0900000000-081f0ec3c9d46b1b3bd82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 30V, Positive-QTOFsplash10-0006-9200000000-050f4f2282bac4a4ede92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 40V, Positive-QTOFsplash10-0006-9000000000-39816589e8ae9e5f86042021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Positive-QTOFsplash10-0udi-0900000000-584bee8b1d116d28ad722016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 20V, Positive-QTOFsplash10-0w2i-0900000000-9b1ca159ad8a687a64492016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 40V, Positive-QTOFsplash10-0ab9-9500000000-8c23a4085269713574de2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Negative-QTOFsplash10-0udi-0900000000-fdc0b46552431f575ba62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 20V, Negative-QTOFsplash10-0pb9-2900000000-280bfbe85df4a0da08942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 40V, Negative-QTOFsplash10-0pbc-9200000000-ca4c67126b692467c9ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Positive-QTOFsplash10-000i-0900000000-7d7c2fb30321be106dba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 20V, Positive-QTOFsplash10-052r-0900000000-5da27f9f442b311a97fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 40V, Positive-QTOFsplash10-0a59-9500000000-02d654c5564e7e65df732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 10V, Negative-QTOFsplash10-0udi-0900000000-222319115ca49603e9d02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 20V, Negative-QTOFsplash10-0a4i-0900000000-2682511e81f9b8e4a1012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-Methyl-4-pyridone-3-carboxamide 40V, Negative-QTOFsplash10-0zfr-9200000000-ecbc5d1685a2efb1bb502021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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 IDM02506
MarkerDB IDNot Available
Good Scents 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