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Showing NP-Card for 1-Methylnicotinamide (NP0000742)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:17:56 UTC
NP-MRD IDNP0000742
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Methylnicotinamide
Description1-Methylnicotinamide is a metabolite of nicotinamide and is produced primarily in the liver. It has anti-inflammatory properties (PMID 16197374 ). It is a product of nicotinamide N-methyltransferase [EC 2.1.1.1] In the pathway of nicotinate and nicotinamide metabolism (KEGG). 1-Methylnicotinamide may be an endogenous activator of prostacyclin production and thus may regulate thrombotic as well as inflammatory processes in the cardiovascular system (PMID: 17641676 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000742 (1-Methylnicotinamide)


  Mrv1652305261923512D          

 10 10  0  0  0  0            999 V2000
    0.2183    0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980   -0.9551    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.2075    0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339    0.2934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176    1.5179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980   -1.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
M  CHG  1   5   1
M  END
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3D MOL for NP0000742 (1-Methylnicotinamide)

HMDB0000699
     RDKit          3D
1-Methylnicotinamide
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.7006   -1.0349    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4987   -0.2685    0.0096 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5680    0.9512   -0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410    1.6998   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    1.1521   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -0.0872    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1925   -0.6599    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.0222    0.2512 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1959   -1.7998    1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2896   -0.7739    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5903   -0.3811    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7785   -1.8157   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -1.5545    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    1.3295   -0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329    2.6704   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873    1.6976   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7658    0.6452    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -0.0621   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.7304    0.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  6 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  8 17  1  0
  8 18  1  0
 10 19  1  0
M  CHG  1   2   1
M  END
Download

3D SDF for NP0000742 (1-Methylnicotinamide)


  Mrv1652305261923512D          

 10 10  0  0  0  0            999 V2000
    0.2183    0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980   -0.9551    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.2075    0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339    0.2934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176    1.5179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980   -1.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
M  CHG  1   5   1
M  END
> <DATABASE_ID>
NP0000742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+]1=CC=CC(=C1)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1

> <INCHI_KEY>
LDHMAVIPBRSVRG-UHFFFAOYSA-O

> <FORMULA>
C7H9N2O

> <MOLECULAR_WEIGHT>
137.1592

> <EXACT_MASS>
137.07148792

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.251177983907619

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carbamoyl-1-methylpyridin-1-ium

> <ALOGPS_LOGP>
-3.72

> <JCHEM_LOGP>
-4.337154676471745

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.235695057499976

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5296412362667113

> <JCHEM_POLAR_SURFACE_AREA>
46.97

> <JCHEM_REFRACTIVITY>
39.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methylnicotinamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000742 (1-Methylnicotinamide)

HMDB0000699
     RDKit          3D
1-Methylnicotinamide
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.7006   -1.0349    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4987   -0.2685    0.0096 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5680    0.9512   -0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410    1.6998   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    1.1521   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -0.0872    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1925   -0.6599    0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.0222    0.2512 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1959   -1.7998    1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2896   -0.7739    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5903   -0.3811    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7785   -1.8157   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -1.5545    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    1.3295   -0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329    2.6704   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873    1.6976   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7658    0.6452    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -0.0621   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.7304    0.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  6 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  8 17  1  0
  8 18  1  0
 10 19  1  0
M  CHG  1   2   1
M  END
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PDB for NP0000742 (1-Methylnicotinamide)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.407   0.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.407  -1.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.930   1.305   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.719   1.312   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.930  -1.783   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0      -2.254   0.541   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.050   0.548   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       1.713   2.833   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.254  -1.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.930  -3.292   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9   10                                                  
CONECT    6    3    9                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5    6                                                       
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0000742 (1-Methylnicotinamide)

COMPND    HMDB0000699
HETATM    1  C1  UNL     1      -2.701  -1.035   0.278  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.499  -0.269   0.010  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.568   0.951  -0.572  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.441   1.700  -0.838  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.781   1.152  -0.484  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.882  -0.087   0.108  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.193  -0.660   0.480  1.00  0.00           C  
HETATM    8  N2  UNL     1       3.395   0.022   0.251  1.00  0.00           N  
HETATM    9  O1  UNL     1       2.196  -1.800   1.019  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.290  -0.774   0.342  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.590  -0.381   0.310  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.779  -1.816  -0.524  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.632  -1.555   1.257  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.567   1.329  -0.827  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.533   2.670  -1.303  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.687   1.698  -0.672  1.00  0.00           H  
HETATM   17  H7  UNL     1       3.766   0.645   1.001  1.00  0.00           H  
HETATM   18  H8  UNL     1       3.939  -0.062  -0.633  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.240  -1.730   0.797  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3   10
CONECT    3    4   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7   10   10
CONECT    7    8    9    9
CONECT    8   17   18
CONECT   10   19
END
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SMILES for NP0000742 (1-Methylnicotinamide)

C[N+]1=CC=CC(=C1)C(N)=O
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INCHI for NP0000742 (1-Methylnicotinamide)

InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1
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View in JSmol
Synonyms
ValueSource
1-Methyl nicotinamideChEBI
1-Methylnicotinamide cationChEBI
3-(Aminocarbonyl)-1-methylpyridiniumChEBI
3-Carbamoyl-1-methylpyridin-1-iumChEBI
N(1)-MethylnicotinamideChEBI
N-1-MethylnicotinamideChEBI
TrigonellinamideChEBI
1-Methyl-3-carbamoylpyridiniumHMDB
1-Methyl-3-carbamoylpyridinium cationHMDB
3-Amido-N-methylpyridinium: 1-methyl-3-pyridinecarboxamideHMDB
3-Carbamoyl-1-methyl-pyridiniumHMDB
I-methyl nicotinamideHMDB
N'-methylnicotinamideHMDB
N'MethylnicotinamideHMDB
N-Methyl-3-carbamidopyridiniumHMDB
N-Methyl-3-carbamoylpyridinium ionHMDB
N1-MethylnicotinamideHMDB
N(1)-Methylnicotinamide chlorideHMDB
N(1)-Methylnicotinamide cyanideHMDB
N(1)-Methylnicotinamide fluorideHMDB
N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeledHMDB
N(1)-Methylnicotinamide methylsulfateHMDB
N(1)-Methylnicotinamide perchlorateHMDB
N(1)-Methylnicotinamide bromideHMDB
N(1)-Methylnicotinamide iodideHMDB
N(1)-Methylnicotinamide tetrafluoroborate (1-)HMDB
Trigonellamide chlorideHMDB
Chemical FormulaC7H9N2O
Average Mass137.1592 Da
Monoisotopic Mass137.07149 Da
IUPAC Name3-carbamoyl-1-methylpyridin-1-ium
Traditional Name1-methylnicotinamide
CAS Registry Number3106-60-3
SMILES
C[N+]1=CC=CC(=C1)C(N)=O
InChI Identifier
InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1
InChI KeyLDHMAVIPBRSVRG-UHFFFAOYSA-O
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-02View Spectrum
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
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
  • N-methylpyridinium
  • Pyridinium
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility855 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP-3.7ALOGPS
logP-4.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)12.24ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.97 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000699
DrugBank IDDB11710
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022188
KNApSAcK IDC00052106
Chemspider ID444
KEGG Compound IDC02918
BioCyc IDCPD-396
BiGG ID2226225
Wikipedia Link1-Methylnicotinamide
METLIN ID5667
PubChem Compound457
PDB IDNot Available
ChEBI ID16797
Good Scents IDNot Available
References
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Pelletier O, Brassard R: Automated and manual determination of N1-methylnicotinamide in urine. Am J Clin Nutr. 1977 Dec;30(12):2108-16. [PubMed:145178 ]
  3. Carter EG: Quantitation of urinary niacin metabolites by reversed-phase liquid chromatography. Am J Clin Nutr. 1982 Nov;36(5):926-30. [PubMed:6215856 ]
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