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Showing NP-Card for N1-Methyl-4-pyridone-3-carboxamide (NP0087151)

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Record Information
Version2.0
Created at2022-05-11 16:41:34 UTC
Updated at2022-05-11 16:41:35 UTC
NP-MRD IDNP0087151
Secondary Accession NumbersNone
Natural Product 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. N1-Methyl-4-pyridone-3-carboxamide was first documented in 1961 (PMID: 13692332). As a uremic toxin, this compound can cause uremic syndrome.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)


  Mrv0541 02231219542D          

 11 11  0  0  0  0            999 V2000
   11.2450   -9.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5306  -10.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740   -9.4262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740  -11.9012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3885  -12.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595   -9.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2450  -11.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595  -10.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740  -11.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595  -12.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2450  -11.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.8272   -0.6933   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065   -0.1335   -0.0351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4442    1.0961    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    1.7390    0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9211    1.0604    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601    1.5323    0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655   -0.2154   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -0.9255   -0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608   -0.3656   -0.2201 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049   -2.0676   -0.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696   -0.7796   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -0.8093    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7309   -1.6598   -0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.0135   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3697    1.6274    0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.7137    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.0645   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282   -0.4212    0.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4681   -1.7758   -0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7 11  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
 11 19  1  0
  9 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)


  Mrv0541 02231219542D          

 11 11  0  0  0  0            999 V2000
   11.2450   -9.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5306  -10.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740   -9.4262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740  -11.9012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3885  -12.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595   -9.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2450  -11.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595  -10.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740  -11.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595  -12.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2450  -11.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087151

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
KTLRWTOPTKGYQY-UHFFFAOYSA-N

> <FORMULA>
C7H8N2O2

> <MOLECULAR_WEIGHT>
152.1506

> <EXACT_MASS>
152.05857751

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.701437263061493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-0.5628999373333334

> <ALOGPS_LOGS>
-0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.726987756581746

> <JCHEM_PKA_STRONGEST_BASIC>
0.3861706170764213

> <JCHEM_POLAR_SURFACE_AREA>
63.4

> <JCHEM_REFRACTIVITY>
40.807599999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-4-oxopyridine-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)

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PDB for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      20.991 -17.596   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.657 -19.905   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      23.658 -17.596   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      23.658 -22.216   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      24.992 -22.985   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.324 -18.365   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.991 -20.676   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.324 -19.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.658 -20.676   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.324 -22.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.991 -22.216   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    5    9   10                                                  
CONECT    5    4                                                            
CONECT    6    1    3    8                                                  
CONECT    7    2    8   11                                                  
CONECT    8    6    7    9                                                  
CONECT    9    4    8                                                       
CONECT   10    4   11                                                       
CONECT   11    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)
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SMILES for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)
CN1C=CC(=O)C(=C1)C(N)=O
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INCHI for NP0087151 (N1-Methyl-4-pyridone-3-carboxamide)
InChI=1S/C7H8N2O2/c1-9-3-2-6(10)5(4-9)7(8)11/h2-4H,1H3,(H2,8,11)
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View in JSmol
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 Mass152.1506 Da
Monoisotopic Mass152.05858 Da
IUPAC Name1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide
Traditional Name1-methyl-4-oxopyridine-3-carboxamide
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0004194  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. CHANG ML, JOHNSON BC: N-Methyl-4-pyridone-5-carboxamide as a metabolite of nicotinic acid in man and monkey. J Biol Chem. 1961 Jul;236:2096-8. [PubMed:13692332  ]