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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:06 UTC

Update Date

2023-02-21 17:16:28 UTC

HMDB ID

HMDB0002730

Secondary Accession Numbers

HMDB02730

Metabolite Identification

Common Name

Nicotinamide N-oxide

Description

Nicotinamide 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Oxide-(8ci)-nicotinamide	HMDB
1-Oxide-3-pyridinecarboxamide	HMDB
1-Oxide-nicotinamide	HMDB
1-Oxy-nicotinamide	HMDB
Nicotinamide 1-oxide	HMDB
Nicotinamide N1-oxide	HMDB
Nicotinamide-N-oxide	HMDB
1-oxo-1Λ⁵-pyridine-3-carboximidate	Generator, HMDB
Nicotinamide N-oxide	MeSH

Chemical Formula

C₆H₆N₂O₂

Average Molecular Weight

138.124

Monoisotopic Molecular Weight

138.042927446

IUPAC Name

3-carbamoylpyridin-1-ium-1-olate

Traditional Name

3-pyridinecarboxamide, 1-oxide

CAS Registry Number

1986-81-8

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 Key

USSFUVKEHXDAPM-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Nicotinamides

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD0-2083 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1491034)

Source

Endogenous

Endogenous (HMDB: HMDB0002730)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	289 - 293 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.66 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.7	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-0.0075	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.67 m³·mol⁻¹	ChemAxon
Polarizability	12.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.019	31661259
DarkChem	[M-H]-	126.06	31661259
DeepCCS	[M+H]+	126.0	30932474
DeepCCS	[M-H]-	123.703	30932474
DeepCCS	[M-2H]-	159.203	30932474
DeepCCS	[M+Na]+	133.384	30932474
AllCCS	[M+H]+	128.7	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	133.1	32859911
AllCCS	[M+Na]+	134.4	32859911
AllCCS	[M-H]-	123.9	32859911
AllCCS	[M+Na-2H]-	125.5	32859911
AllCCS	[M+HCOO]-	127.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.57 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2305 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	311.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	528.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	339.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	47.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	210.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	98.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	230.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	798.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	593.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	43.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	706.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	657.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	382.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	285.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicotinamide N-oxide	NC(=O)C1=C[N+]([O-])=CC=C1	2655.4	Standard polar	33892256
Nicotinamide N-oxide	NC(=O)C1=C[N+]([O-])=CC=C1	1457.9	Standard non polar	33892256
Nicotinamide N-oxide	NC(=O)C1=C[N+]([O-])=CC=C1	1799.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nicotinamide N-oxide,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C1	1631.1	Semi standard non polar	33892256
Nicotinamide N-oxide,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C1	1615.4	Standard non polar	33892256
Nicotinamide N-oxide,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C1	1878.6	Standard polar	33892256
Nicotinamide N-oxide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C	1695.3	Semi standard non polar	33892256
Nicotinamide N-oxide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C	1622.5	Standard non polar	33892256
Nicotinamide N-oxide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C	1830.4	Standard polar	33892256
Nicotinamide N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C1	1897.3	Semi standard non polar	33892256
Nicotinamide N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C1	1759.1	Standard non polar	33892256
Nicotinamide N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([O-])=C1	2024.3	Standard polar	33892256
Nicotinamide N-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C(C)(C)C	2169.6	Semi standard non polar	33892256
Nicotinamide N-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C(C)(C)C	2025.5	Standard non polar	33892256
Nicotinamide N-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([O-])=C1)[Si](C)(C)C(C)(C)C	2023.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-7900000000-3d46187b05469bec6274	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Positive-QTOF	splash10-000i-0900000000-c90ecde2662af2b1c341	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Positive-QTOF	splash10-002s-9400000000-b790948a06b72ff51ca6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Positive-QTOF	splash10-03di-9100000000-4b23fbf313e902a9822b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Negative-QTOF	splash10-000i-0900000000-11fc9d3b70e386ed9c27	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Negative-QTOF	splash10-000i-0900000000-05a167832ffbbeb9e515	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Negative-QTOF	splash10-00kr-8900000000-b66c96207c87c2e4d83e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Positive-QTOF	splash10-000i-0900000000-77e9b6ee9f303c0ee032	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Positive-QTOF	splash10-100a-9400000000-b5c3b98e54a7a808fe6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Positive-QTOF	splash10-0udi-9000000000-dfdd892a72902816587e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 10V, Negative-QTOF	splash10-000i-0900000000-a17c3f84530444f730d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 20V, Negative-QTOF	splash10-000i-1900000000-f30b4ed79b4ba9f1d895	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide N-oxide 40V, Negative-QTOF	splash10-0gbc-9100000000-f3304098a42ed972fd2f	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	283 +/- 4.3 uM	Adult (>18 years old)	Not Specified	Normal	1491034	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023057

KNApSAcK ID

Not Available

Chemspider ID

65522

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

1503

PubChem Compound

72661

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Liu, Zhenxiang; Cai, Chun. Synthesis of 2-chloronicotinonitrile. Jingxi Huagong Zhongjianti (2005), 35(3), 28-30.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]

Showing metabocard for Nicotinamide N-oxide (HMDB0002730)

MOL for HMDB0002730 (Nicotinamide N-oxide)

3D MOL for HMDB0002730 (Nicotinamide N-oxide)

3D SDF for HMDB0002730 (Nicotinamide N-oxide)

3D-SDF for HMDB0002730 (Nicotinamide N-oxide)

PDB for HMDB0002730 (Nicotinamide N-oxide)

3D PDB for HMDB0002730 (Nicotinamide N-oxide)

SMILES for HMDB0002730 (Nicotinamide N-oxide)

INCHI for HMDB0002730 (Nicotinamide N-oxide)

Structure for HMDB0002730 (Nicotinamide N-oxide)

3D Structure for HMDB0002730 (Nicotinamide N-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra