Showing metabocard for 1-Methylnicotinamide (BMDB0000699)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:07 UTC
Update Date2020-05-21 16:28:55 UTC
BMDB IDBMDB0000699
Secondary Accession Numbers
  • BMDB00699
Metabolite Identification
Common Name1-Methylnicotinamide
Description1-Methylnicotinamide, also known as 1-methylnicotinamide or 1-methylnicotinamide, 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. 1-Methylnicotinamide is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylnicotinamide exists in all living species, ranging from bacteria to humans. 1-Methylnicotinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and 1-methylnicotinamide can be biosynthesized from S-adenosylmethionine and niacinamide; which is catalyzed by the enzyme nicotinamide N-methyltransferase. In addition, 1-Methylnicotinamide can be converted into N1-methyl-2-pyridone-5-carboxamide through the action of the enzyme aldehyde oxidase. In cattle, 1-methylnicotinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Molecular Weight137.1592
Monoisotopic Molecular Weight137.07148792
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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000699
DrugBank IDDB11710
Phenol Explorer Compound IDNot Available
FooDB 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
References
Synthesis ReferenceNelis, Hans J. C. F.; Airy, Subhash C.; Sinsheimer, J. E. Comparison of the alkylation of nicotinamide and 4-(p-nitrobenzyl)pyridine for the determination of aliphatic epoxides. Analytical Chemistry (1982), 54(2), 213-16.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phenylethanolamine N-methyltransferase
General function:
Involved in phenylethanolamine N-methyltransferase acti
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P10938
Molecular weight:
30918.0
Reactions
S-Adenosylmethionine + Niacinamide → S-Adenosylhomocysteine + 1-Methylnicotinamidedetails
Enzyme Details
2. Aldehyde oxidase 1
General function:
Nucleotide transport and metabolism
Specific function:
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:
AOX1
Uniprot ID:
P48034
Molecular weight:
147611.0
Reactions
1-Methylnicotinamide + Oxygen + Water → N1-Methyl-2-pyridone-5-carboxamide + Hydrogen peroxidedetails
1-Methylnicotinamide + Water + Oxygen → N1-Methyl-4-pyridone-3-carboxamide + Hydrogen peroxidedetails