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Record Information
Version5.0
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 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 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make nicotinamide N-oxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Nicotinamide N-oxide.
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, HMDB
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 Molecular Properties
PropertyValueReference
Melting Point289 - 293 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.01931661259
DarkChem[M-H]-126.0631661259
DeepCCS[M+H]+126.030932474
DeepCCS[M-H]-123.70330932474
DeepCCS[M-2H]-159.20330932474
DeepCCS[M+Na]+133.38430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nicotinamide N-oxideNC(=O)C1=C[N+]([O-])=CC=C12655.4Standard polar33892256
Nicotinamide N-oxideNC(=O)C1=C[N+]([O-])=CC=C11457.9Standard non polar33892256
Nicotinamide N-oxideNC(=O)C1=C[N+]([O-])=CC=C11799.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nicotinamide N-oxide,1TMS,isomer #1C[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C11631.1Semi standard non polar33892256
Nicotinamide N-oxide,1TMS,isomer #1C[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C11615.4Standard non polar33892256
Nicotinamide N-oxide,1TMS,isomer #1C[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C11878.6Standard polar33892256
Nicotinamide N-oxide,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C1695.3Semi standard non polar33892256
Nicotinamide N-oxide,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C1622.5Standard non polar33892256
Nicotinamide N-oxide,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C1830.4Standard polar33892256
Nicotinamide N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C11897.3Semi standard non polar33892256
Nicotinamide N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C11759.1Standard non polar33892256
Nicotinamide N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C12024.3Standard polar33892256
Nicotinamide N-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C(C)(C)C2169.6Semi standard non polar33892256
Nicotinamide N-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C(C)(C)C2025.5Standard non polar33892256
Nicotinamide N-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C(C)(C)C2023.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinamide N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7900000000-3d46187b05469bec62742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinamide N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinamide N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Positive-QTOFsplash10-000i-0900000000-c90ecde2662af2b1c3412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Positive-QTOFsplash10-002s-9400000000-b790948a06b72ff51ca62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Positive-QTOFsplash10-03di-9100000000-4b23fbf313e902a9822b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Negative-QTOFsplash10-000i-0900000000-11fc9d3b70e386ed9c272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Negative-QTOFsplash10-000i-0900000000-05a167832ffbbeb9e5152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Negative-QTOFsplash10-00kr-8900000000-b66c96207c87c2e4d83e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Positive-QTOFsplash10-000i-0900000000-77e9b6ee9f303c0ee0322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Positive-QTOFsplash10-100a-9400000000-b5c3b98e54a7a808fe6f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Positive-QTOFsplash10-0udi-9000000000-dfdd892a72902816587e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Negative-QTOFsplash10-000i-0900000000-a17c3f84530444f730d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Negative-QTOFsplash10-000i-1900000000-f30b4ed79b4ba9f1d8952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Negative-QTOFsplash10-0gbc-9100000000-f3304098a42ed972fd2f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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 ]