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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:06 UTC
Update Date2020-02-26 21:24:15 UTC
HMDB IDHMDB0002730
Secondary Accession Numbers
  • HMDB02730
Metabolite Identification
Common NameNicotinamide N-oxide
DescriptionNicotinamide N-oxide, also known as 1-oxide-nicotinamide, 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. Nicotinamide N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752255
Synonyms
ValueSource
1-Oxide-(8ci)-nicotinamideHMDB
1-Oxide-3-pyridinecarboxamideHMDB
1-Oxide-nicotinamideHMDB
1-Oxy-nicotinamideHMDB
Nicotinamide 1-oxideHMDB
Nicotinamide N1-oxideHMDB
Nicotinamide-N-oxideHMDB
1-oxo-1Λ⁵-pyridine-3-carboximidateGenerator
Nicotinamide N-oxideMeSH
Chemical FormulaC6H6N2O2
Average Molecular Weight138.124
Monoisotopic Molecular Weight138.042927446
IUPAC Name3-carbamoylpyridin-1-ium-1-olate
Traditional Name3-pyridinecarboxamide, 1-oxide
CAS Registry Number1986-81-8
SMILES
NC(=O)C1=C[N+]([O-])=CC=C1
InChI Identifier
InChI=1S/C6H6N2O2/c7-6(9)5-2-1-3-8(10)4-5/h1-4H,(H2,7,9)
InChI KeyUSSFUVKEHXDAPM-UHFFFAOYSA-N
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
  • Azacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • 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
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point289 - 293 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.66 g/LALOGPS
logP-1.1ALOGPS
logP-1.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-0.0075ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.67 m³·mol⁻¹ChemAxon
Polarizability12.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7900000000-3d46187b05469bec6274Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c90ecde2662af2b1c341Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002s-9400000000-b790948a06b72ff51ca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9100000000-4b23fbf313e902a9822bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-11fc9d3b70e386ed9c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-05a167832ffbbeb9e515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-8900000000-b66c96207c87c2e4d83eSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified283 +/- 4.3 uMAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023057
KNApSAcK IDNot Available
Chemspider ID65522
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID1503
PubChem Compound72661
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceLiu, Zhenxiang; Cai, Chun. Synthesis of 2-chloronicotinonitrile. Jingxi Huagong Zhongjianti (2005), 35(3), 28-30.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mrochek JE, Jolley RL, Young DS, Turner WJ: Metabolic response of humans to ingestion of nicotinic acid and nicotinamide. Clin Chem. 1976 Nov;22(11):1821-7. [PubMed:135660 ]