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Showing NP-Card for N-Methylnicotinamide (NP0000261)

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Record Information
Version1.0
Created at2006-05-22 15:12:36 UTC
Updated at2021-10-07 20:40:57 UTC
NP-MRD IDNP0000261
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methylnicotinamide
DescriptionN-methylnicotinamide (NMA), also known as Nicotinyl methylamide or N-methylniacinamide, 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. N-methylnicotinamide is also classified as a pyridinecarboxamide, which consists a pyridine group attached to a carboxamide moiety. More specifically, N-methylnicotinamide is nicotinamide in which one of the amide hydrogens in the carboxamide group is substituted by a methyl group. Note that N-methylnicotinamide is structurally and functionally different than N(1)-methylnicotinamide (also called 1-methylnicotinamide). Unfortunately, there is extensive confusion and mis-labeling of N-methylnicotinamide and N(1)-methylnicotinamide in the scientific literature. N-methylnicotinamide is a metabolite of niacin (vitamin B3 or nicotinamide) and is commonly found in human urine. Low levels of urinary excretion of N-methylnicotinamide can indicate a niacin deficiency. In patients with liver cirrhosis, nicotinamide methylation is increased which can lead to a rise in urinary N-methylnicotinamide (PMID: 11316167 ). Increased methylation of nicotinamide in cirrhosis patients might play a protective role against the toxic effects of intracellular accumulation of nicotinamide deriving from the catabolic state of cirrhosis (PMID: 11316167 ). N-methylnicotinamide is known to inhibit choline transport and reduce choline clearance out of the brain. N-methylnicotinamide has been shown to improve endothelial dysfunction and to attenuate atherogenesis via the modulation of asymmetric dimethylarginine (ADMA) and dimethylarginine dimethylaminohydrolase (PMID: 26887666 ). N-methylnicotinamide significantly increases nitric oxide/cyclic guanosinemonophosphate levels and decreases asymmetric dimethylarginine (ADMA) concentrations by induction of dimethylarginine dimethylaminohydrolase (DDAH) both in aorta and endothelial cells. N-methylnicotinamide has also been identified as a microbial metabolite.
Structure
Data?1628978392
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000261 (N-Methylnicotinamide)


  Mrv1652308142123492D          

 10 10  0  0  0  0            999 V2000
   21.7327  -15.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -15.9637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7327  -18.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -15.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4470  -16.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4470  -17.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7327  -17.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4470  -18.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -17.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -18.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for NP0000261 (N-Methylnicotinamide)

HMDB0003152
     RDKit          3D
N-Methylnicotinamide
 18 18  0  0  0  0  0  0  0  0999 V2000
    3.2992    0.4714   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    0.5288    0.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761   -0.2196   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648   -0.9796   -1.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786   -0.1394   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -0.8971   -0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.8844   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079   -0.0560    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    0.6953    1.5006 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8528    0.6604    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729   -0.4675   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    1.3807   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606    0.4640   -1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    1.1647    0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2529   -1.5401   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6005   -1.4691   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017    0.0115    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    1.2760    1.5318 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0000261 (N-Methylnicotinamide)


  Mrv1652308142123492D          

 10 10  0  0  0  0            999 V2000
   21.7327  -15.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -15.9637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7327  -18.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -15.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4470  -16.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4470  -17.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7327  -17.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4470  -18.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -17.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1615  -18.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(=O)C1=CN=CC=C1

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

> <INCHI_KEY>
ZYVXHFWBYUDDBM-UHFFFAOYSA-N

> <FORMULA>
C7H8N2O

> <MOLECULAR_WEIGHT>
136.1512

> <EXACT_MASS>
136.063662888

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.865233788543083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methylpyridine-3-carboxamide

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-0.17011025099999968

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.749769804133646

> <JCHEM_PKA_STRONGEST_BASIC>
3.6226282895542377

> <JCHEM_POLAR_SURFACE_AREA>
41.99

> <JCHEM_REFRACTIVITY>
37.8762

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N'methylnicotinamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000261 (N-Methylnicotinamide)

HMDB0003152
     RDKit          3D
N-Methylnicotinamide
 18 18  0  0  0  0  0  0  0  0999 V2000
    3.2992    0.4714   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    0.5288    0.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761   -0.2196   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648   -0.9796   -1.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786   -0.1394   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -0.8971   -0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.8844   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079   -0.0560    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    0.6953    1.5006 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8528    0.6604    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729   -0.4675   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    1.3807   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606    0.4640   -1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    1.1647    0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2529   -1.5401   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6005   -1.4691   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017    0.0115    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    1.2760    1.5318 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0000261 (N-Methylnicotinamide)

HEADER    PROTEIN                                 14-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-AUG-21         0                                  
HETATM    1  O   UNK     0      40.568 -29.799   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      43.235 -29.799   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      40.568 -34.419   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      43.235 -28.259   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      41.901 -30.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.901 -32.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      40.568 -32.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.901 -35.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      43.235 -32.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.235 -34.419   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    4    5                                                       
CONECT    3    7    8                                                       
CONECT    4    2                                                            
CONECT    5    1    2    6                                                  
CONECT    6    5    7    9                                                  
CONECT    7    3    6                                                       
CONECT    8    3   10                                                       
CONECT    9    6   10                                                       
CONECT   10    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0000261 (N-Methylnicotinamide)

COMPND    HMDB0003152
HETATM    1  C1  UNL     1       3.299   0.471  -0.479  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.938   0.529   0.018  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.876  -0.220  -0.523  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.165  -0.980  -1.503  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.479  -0.139  -0.001  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.507  -0.897  -0.562  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.801  -0.884  -0.139  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.108  -0.056   0.927  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.144   0.695   1.501  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.853   0.660   1.052  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.773  -0.467  -0.170  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.866   1.381  -0.215  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.261   0.464  -1.608  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.762   1.165   0.818  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.253  -1.540  -1.394  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.601  -1.469  -0.570  1.00  0.00           H  
HETATM   17  H7  UNL     1      -4.102   0.011   1.319  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.093   1.276   1.532  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   10
CONECT   10   18
END
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SMILES for NP0000261 (N-Methylnicotinamide)

CNC(=O)C1=CN=CC=C1
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INCHI for NP0000261 (N-Methylnicotinamide)

InChI=1S/C7H8N2O/c1-8-7(10)6-3-2-4-9-5-6/h2-5H,1H3,(H,8,10)
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View in JSmol
Synonyms
ValueSource
3-(Methylcarbamoyl)pyridineChEBI
3-(N-Methylcarbamoyl)pyridineChEBI
N-Methyl nicotineamideChEBI
N-Methyl-3-pyridinecarboxamideChEBI
N-Methylpyridine-3-carboxamideChEBI
Nicotinic acid methylamideChEBI
Nicotinate methylamideGenerator
N-METHYL-nicotinamideHMDB
N-Methylnicotinamide monohydrochlorideHMDB
N -Methyl nicotineamideHMDB
Chemical FormulaC7H8N2O
Average Mass136.1512 Da
Monoisotopic Mass136.06366 Da
IUPAC NameN-methylpyridine-3-carboxamide
Traditional NameN'methylnicotinamide
CAS Registry Number114-33-0
SMILES
CNC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C7H8N2O/c1-8-7(10)6-3-2-4-9-5-6/h2-5H,1H3,(H,8,10)
InChI KeyZYVXHFWBYUDDBM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)V.dorna832021-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-05View 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
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
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point103.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.00Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.21ALOGPS
logP-0.17ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)13.75ChemAxon
pKa (Strongest Basic)3.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.88 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003152
DrugBank IDDB08840
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023115
KNApSAcK IDNot Available
Chemspider ID58476
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNicotinyl_methylamide
METLIN IDNot Available
PubChem Compound64950
PDB IDNot Available
ChEBI ID64399
Good Scents IDNot Available
References
General References
  1. Pumpo R, Sarnelli G, Spinella A, Budillon G, Cuomo R: The metabolism of nicotinamide in human liver cirrhosis: a study on N-methylnicotinamide and 2-pyridone-5-carboxamide production. Am J Gastroenterol. 2001 Apr;96(4):1183-7. [PubMed:11316167 ]
  2. Aleinik SI, Kodentsiva VM, Mitin IE, Sokol'nikov AA, Vrzhesinskaia OA, Isaeva VA, Terekhina TA, Stroganova AS, Erzhen K, Tsibul'skaia OA, et al.: [Effects of the use of a multivitamin preparation "Pikovit" (KRKA, Yugoslavia) on providing nursery children with vitamins]. Vopr Pitan. 1992 May-Jun;(3):14-9. [PubMed:1387494 ]
  3. Varnakova GM: [Use of nicotinamide for correcting the disordered nicotinic acid allowance of patients with noncoronarogenic heart diseases]. Vopr Pitan. 1983 Jul-Aug;(4):32-5. [PubMed:6226157 ]
  4. Cuomo R, Pumpo R, Sarnelli G, Capuano G, Budillon G: Nicotinamide methylation and hepatic energy reserve: a study by liver perfusion in vitro. J Hepatol. 1995 Oct;23(4):465-70. [PubMed:8655965 ]
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