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Human Metabolome Database Version 3.5

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Showing metabocard for N-Methylnicotinamide (HMDB03152)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:36 -0600
Update Date 2013-02-08 17:12:19 -0700
HMDB ID HMDB03152
Secondary Accession Numbers None
Metabolite Identification
Common Name N-Methylnicotinamide
Description N-methylnicotinamide is a metabolite of niacin (or nicotinamide) and is commonly found in human urine. However low levels of urinary excretion of N-methylnicotinamide indicates niacin deficiency. (PMID: 16207585 Link_out). In patients with liver cirrhosis nicotinamide methylation is increased leading to a rise in urinary N-methylnicotinamide. The hyperfunction of this methylating pathway might play a protective role against the toxic effect of intracellular accumulation of nicotinamide deriving from the catabolic state of cirrhosis. N-methylnicotinamide is known to inhibit choline transport and reduce choline clearance out of the brain.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-(Methylcarbamoyl)pyridine
  2. 3-(N-Methylcarbamoyl)pyridine
  3. N -Methyl nicotineamide
  4. N-Methyl-3-pyridinecarboxamide
  5. N-Methylnicotinamide
  6. Nicotinic acid methylamide
Chemical Formula C7H8N2O
Average Molecular Weight 136.1512
Monoisotopic Molecular Weight 136.063662888
IUPAC Name N-methylpyridine-3-carboxamide
Traditional IUPAC Name N-methylnicotinamide
CAS Registry Number 114-33-0
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 Key ZYVXHFWBYUDDBM-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Pyridines and Derivatives
Sub Class Pyridinecarboxamides
Other Descriptors
  • Pyridines and Derivatives
Substituents
  • Carboxamide Group
  • Secondary Carboxylic Acid Amide
Direct Parent Pyridinecarboxamides
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Electron donor
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 103.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 0.00 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 18.6 g/L ALOGPS
LogP -0.21 ALOGPS
LogP -0.17 ChemAxon
LogS -0.87 ALOGPS
pKa (strongest acidic) 13.75 ChemAxon
pKa (strongest basic) 3.62 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 41.99 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 37.88 ChemAxon
Polarizability 13.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Type 2 Diabetes Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023115
KNApSAcK ID Not Available
Chemspider ID 58476 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03152 Link_out
Metagene Link HMDB03152 Link_out
METLIN ID Not Available
PubChem Compound 64950 Link_out
PDB ID Not Available
ChEBI ID 64399 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out