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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 15:12:36 UTC

Update Date

2023-02-21 17:16:33 UTC

HMDB ID

HMDB0003152

Secondary Accession Numbers

HMDB03152

Metabolite Identification

Common Name

N-Methylnicotinamide

Description

N-methylnicotinamide is a pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group. 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 ). 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. N-methylnicotinamide has been found to be a microbial metabolite.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(Methylcarbamoyl)pyridine	ChEBI
3-(N-Methylcarbamoyl)pyridine	ChEBI
N-Methyl nicotineamide	ChEBI
N-Methyl-3-pyridinecarboxamide	ChEBI
N-Methylpyridine-3-carboxamide	ChEBI
Nicotinic acid methylamide	ChEBI
Nicotinate methylamide	Generator
N -Methyl nicotineamide	HMDB
N-METHYL-nicotinamide	MeSH, HMDB
N-Methylnicotinamide monohydrochloride	MeSH, HMDB

Chemical Formula

C₇H₈N₂O

Average Molecular Weight

136.1512

Monoisotopic Molecular Weight

136.063662888

IUPAC Name

N-methylpyridine-3-carboxamide

Traditional Name

N'methylnicotinamide

CAS Registry Number

114-33-0

SMILES

CN=C(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

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
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
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

pyridinecarboxamide (CHEBI:64399 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0003152)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0003152)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003152)

Source

Endogenous

Endogenous (HMDB: HMDB0003152)

Microbe

Microbe (HMDB: HMDB0003152)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003152)

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	0.65	ALOGPS
logP	-0.17	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	3.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.88 m³·mol⁻¹	ChemAxon
Polarizability	13.87 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]+	128.709	31661259
DarkChem	[M-H]-	124.71	31661259
DeepCCS	[M+H]+	128.442	30932474
DeepCCS	[M-H]-	124.978	30932474
DeepCCS	[M-2H]-	162.144	30932474
DeepCCS	[M+Na]+	137.543	30932474
AllCCS	[M+H]+	128.7	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	133.1	32859911
AllCCS	[M+Na]+	134.3	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	131.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methylnicotinamide	CNC(=O)C1=CN=CC=C1	2110.9	Standard polar	33892256
N-Methylnicotinamide	CNC(=O)C1=CN=CC=C1	1466.3	Standard non polar	33892256
N-Methylnicotinamide	CNC(=O)C1=CN=CC=C1	1441.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methylnicotinamide,1TMS,isomer #1	CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C	1414.4	Semi standard non polar	33892256
N-Methylnicotinamide,1TMS,isomer #1	CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C	1437.8	Standard non polar	33892256
N-Methylnicotinamide,1TMS,isomer #1	CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C	1788.0	Standard polar	33892256
N-Methylnicotinamide,1TBDMS,isomer #1	CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	1659.3	Semi standard non polar	33892256
N-Methylnicotinamide,1TBDMS,isomer #1	CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	1647.0	Standard non polar	33892256
N-Methylnicotinamide,1TBDMS,isomer #1	CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	1956.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylnicotinamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-94cc770fe8f431a31a23	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylnicotinamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylnicotinamide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOF	splash10-001i-9400000000-8e4f49b47197c2f4950a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOF	splash10-000i-1900000000-2152d45cdd5d4a662a0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOF	splash10-0ue9-9000000000-56e1f859bab88518e234	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOF	splash10-000i-1900000000-9ca26f496c6a3a243dd0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOF	splash10-0ue9-9000000000-b8d9c720208f33d56554	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOF	splash10-001i-9300000000-0c8c3a9a6ea309d68dcd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Negative-QTOF	splash10-004i-9000000000-388b45f56c914aef2c66	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Negative-QTOF	splash10-004i-9100000000-5a24140875f7746c8f25	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Negative-QTOF	splash10-0ufr-9000000000-9e2091f72eb24ecdce6c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOF	splash10-000i-0900000000-dfdfbb6805540661146c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOF	splash10-000i-2900000000-a85e482755a0e7a2fbbb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOF	splash10-0kai-9100000000-c695203a7da9f4d2ee3e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Negative-QTOF	splash10-000i-0900000000-0ccdb864a51adc6731d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Negative-QTOF	splash10-052r-3900000000-aa587304320e04d3f4ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Negative-QTOF	splash10-004i-9000000000-458b5a3c154373324d86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Negative-QTOF	splash10-004r-9600000000-8c19f57e019ee89463af	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Negative-QTOF	splash10-004i-9000000000-d55af7b467802be46f89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOF	splash10-000i-0900000000-f77bf0c7af614dc22705	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOF	splash10-06sr-9800000000-642378e25bf582bc8ff2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOF	splash10-0fb9-9000000000-01d687f29b752dd7b293	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	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+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

Cytoplasm (predicted from logP)

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Type 2 Diabetes	17190852	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL: A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiol Genomics. 2007 Apr 24;29(2):99-108. Epub 2006 Dec 26. [PubMed:17190852 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

DB08840

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023115

KNApSAcK ID

Not Available

Chemspider ID

58476

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nicotinyl_methylamide

METLIN ID

Not Available

PubChem Compound

64950

PDB ID

Not Available

ChEBI ID

64399

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
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 ]
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 ]
Pitche PT: [Pellagra]. Sante. 2005 Jul-Sep;15(3):205-8. [PubMed:16207585 ]
Jiang N, Wang M, Song J, Liu Y, Chen H, Mu D, Xia M: N-methylnicotinamide protects against endothelial dysfunction and attenuates atherogenesis in apolipoprotein E-deficient mice. Mol Nutr Food Res. 2016 Jul;60(7):1625-36. doi: 10.1002/mnfr.201501019. Epub 2016 May 4. [PubMed:26887666 ]

Showing metabocard for N-Methylnicotinamide (HMDB0003152)

MOL for HMDB0003152 (N-Methylnicotinamide)

3D MOL for HMDB0003152 (N-Methylnicotinamide)

3D SDF for HMDB0003152 (N-Methylnicotinamide)

3D-SDF for HMDB0003152 (N-Methylnicotinamide)

PDB for HMDB0003152 (N-Methylnicotinamide)

3D PDB for HMDB0003152 (N-Methylnicotinamide)

SMILES for HMDB0003152 (N-Methylnicotinamide)

INCHI for HMDB0003152 (N-Methylnicotinamide)

Structure for HMDB0003152 (N-Methylnicotinamide)

3D Structure for HMDB0003152 (N-Methylnicotinamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra