Human Metabolome Database: Showing metabocard for 1-Methylnicotinamide (HMDB0000699)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2018-05-20 09:40:03 UTC

HMDB ID

HMDB0000699

Secondary Accession Numbers

HMDB00699

Metabolite Identification

Common Name

1-Methylnicotinamide

Description

1-Methylnicotinamide is a metabolite of nicotinamide and is produced primarily in the liver. It has anti-inflammatory properties (PMID 16197374 ). It is a product of nicotinamide N-methyltransferase [EC 2.1.1.1] in the pathway of nicotinate and nicotinamide metabolism (KEGG). 1-Methylnicotinamide may be an endogenous activator of prostacyclin production and thus may regulate thrombotic as well as inflammatory processes in the cardiovascular system (PMID: 17641676 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Methylnicotinamide cation	ChEBI
3-(Aminocarbonyl)-1-methylpyridinium	ChEBI
N(1)-Methylnicotinamide	ChEBI
Trigonellinamide	ChEBI
1-Methyl-3-carbamoylpyridinium	HMDB
1-Methyl-3-carbamoylpyridinium cation	HMDB
3-amido-N-Methylpyridinium: 1-methyl-3-pyridinecarboxamide	HMDB
3-Carbamoyl-1-methyl-pyridinium	HMDB
I-methyl nicotinamide	HMDB
N'-methylnicotinamide	HMDB
N'Methylnicotinamide	HMDB
N-1-Methylnicotinamide	HMDB
N-Methyl-3-carbamidopyridinium	HMDB
N-Methyl-3-carbamoylpyridinium ion	HMDB
N1-Methylnicotinamide	HMDB
N(1)-Methylnicotinamide chloride	MeSH
N(1)-Methylnicotinamide cyanide	MeSH
N(1)-Methylnicotinamide fluoride	MeSH
N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeled	MeSH
N(1)-Methylnicotinamide methylsulfate	MeSH
N(1)-Methylnicotinamide perchlorate	MeSH
N(1)-Methylnicotinamide bromide	MeSH
N(1)-Methylnicotinamide iodide	MeSH
N(1)-Methylnicotinamide tetrafluoroborate (1-)	MeSH

Chemical Formula

C₇H₉N₂O

Average Molecular Weight

137.1592

Monoisotopic Molecular Weight

137.07148792

IUPAC Name

3-carbamoyl-1-methylpyridin-1-ium

Traditional Name

1-methylnicotinamide

CAS Registry Number

3106-60-3

SMILES

C[N+]1=CC=CC(=C1)C(N)=O

InChI Identifier

InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1

InChI Key

LDHMAVIPBRSVRG-UHFFFAOYSA-O

Chemical Taxonomy

Description

This compound 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
N-methylpyridinium
Pyridinium
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridinium ion (CHEBI:16797 )
a small molecule (CPD-396 )

Ontology

Physiological effect

Health effect:

Health condition:

Pellagra

Cancer:

Lung cancer

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Nicotinate and Nicotinamide Metabolism

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	855 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	-3.7	ALOGPS
logP	-4.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.13 m³·mol⁻¹	ChemAxon
Polarizability	14.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5900000000-5a5fd45836c387d92371	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-c99e0e70357eb6fa74bb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-93675f2b9efbaba4d471	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fvl-9000000000-b1e908db583e418c2545	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-0900000000-9c3104d60f21f6375b0c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-e500f262d42edb9b3ad7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9200000000-496b2cf62a07bea4f746	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-002f-9000000000-a17b3a63979577f6fa9e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00ou-9000000000-46a856cd097a7a14dc90	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000l-6900000000-360fb882a925f7e9edc9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0006-9000000000-babd4e89db309a5c74cf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-9c3104d60f21f6375b0c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-e500f262d42edb9b3ad7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9200000000-052c844f974abba065eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002f-9000000000-a17b3a63979577f6fa9e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00ou-9000000000-2fe6c195129f32a62a3c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000l-6900000000-360fb882a925f7e9edc9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9000000000-babd4e89db309a5c74cf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0900000000-08a578fa81c8d41a4fe6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-d889aade6d1014ffb393	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-1900000000-8052aba6067c868e594f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9500000000-579bc8310420ec3d8786	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-141e3a418b748abf9e1d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-33499eeb5abff5a8b53b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e45f804a013c97310f00	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Nicotinate and Nicotinamide Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.430 (0.007-0.850) uM	Adult (>18 years old)	Both	Normal	11199218	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	7.749 +/- 7.16 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	0.82 (0.26-2.3) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	1.9 (0.67-5.1) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	3.5 (1.3-6.0) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	4.8 (1.86-13.94) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	6.105 (0.240-12.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	11199218	details
Urine	Detected and Quantified	2.5 (2.1-2.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17709435	details
Urine	Detected and Quantified	5.8 (1.2-15.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.099-0.851 uM	Adult (>18 years old)	Both	Cirrhosis	2142586	details
Urine	Detected and Quantified	7.426 +/- 3.509 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	3.0 (0.0-14.0) umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	22157537	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	21389975	details
Urine	Detected and Quantified	37.00 (11.5-62.7) umol/mmol creatinine	Adult (>18 years old)	Both	Pellagra	17709435	details

Associated Disorders and Diseases

Disease References

Autosomal dominant polycystic kidney disease
Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Cirrhosis
Somogyi A, Siebert D, Bochner F: Determination of endogenous concentrations of N1-methylnicotinamide in human plasma and urine by high-performance liquid chromatography. Anal Biochem. 1990 May 15;187(1):160-5. [PubMed:2142586 ]
Lung Cancer
Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
Pellagra
Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [PubMed:17709435 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

211980 (Lung Cancer)
601313 (Autosomal dominant polycystic kidney disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022188

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

5667

PubChem Compound

457

PDB ID

Not Available

ChEBI ID

16797

References

Synthesis Reference

Nelis, Hans J. C. F.; Airy, Subhash C.; Sinsheimer, J. E. Comparison of the alkylation of nicotinamide and 4-(p-nitrobenzyl)pyridine for the determination of aliphatic epoxides. Analytical Chemistry (1982), 54(2), 213-16.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Pelletier O, Brassard R: Automated and manual determination of N1-methylnicotinamide in urine. Am J Clin Nutr. 1977 Dec;30(12):2108-16. [PubMed:145178 ]
Carter EG: Quantitation of urinary niacin metabolites by reversed-phase liquid chromatography. Am J Clin Nutr. 1982 Nov;36(5):926-30. [PubMed:6215856 ]
Slominska EM, Smolenski RT, Szolkiewicz M, Leaver N, Rutkowski B, Simmonds HA, Swierczynski J: Accumulation of plasma N-methyl-2-pyridone-5-carboxamide in patients with chronic renal failure. Mol Cell Biochem. 2002 Feb;231(1-2):83-8. [PubMed:11952169 ]
Patterson JI, Brown RR, Linkswiler H, Harper AE: Excretion of tryptophan-niacin metabolites by young men: effects of tryptophan, leucine, and vitamin B6 intakes. Am J Clin Nutr. 1980 Oct;33(10):2157-67. [PubMed:6448542 ]
Musfeld C, Biollaz J, Belaz N, Kesselring UW, Decosterd LA: Validation of an HPLC method for the determination of urinary and plasma levels of N1-methylnicotinamide, an endogenous marker of renal cationic transport and plasma flow. J Pharm Biomed Anal. 2001 Jan;24(3):391-404. [PubMed:11199218 ]
Wozniacka A, Wieczorkowska M, Gebicki J, Sysa-Jedrzejowska A: Topical application of 1-methylnicotinamide in the treatment of rosacea: a pilot study. Clin Exp Dermatol. 2005 Nov;30(6):632-5. [PubMed:16197374 ]
Chlopicki S, Swies J, Mogielnicki A, Buczko W, Bartus M, Lomnicka M, Adamus J, Gebicki J: 1-Methylnicotinamide (MNA), a primary metabolite of nicotinamide, exerts anti-thrombotic activity mediated by a cyclooxygenase-2/prostacyclin pathway. Br J Pharmacol. 2007 Sep;152(2):230-9. Epub 2007 Jul 16. [PubMed:17641676 ]

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Reactions

1-Methylnicotinamide + Oxygen + Water → N1-Methyl-4-pyridone-3-carboxamide + Hydrogen peroxide + Hydrogen Ion	details
1-Methylnicotinamide + Oxygen + Water → N1-Methyl-2-pyridone-5-carboxamide + Hydrogen peroxide + Hydrogen Ion	details

Enzyme Details

2. Nicotinamide N-methyltransferase

General function:: Involved in methyltransferase activity
Specific function:: Catalyzes the N-methylation of nicotinamide and other pyridines to form pyridinium ions. This activity is important for biotransformation of many drugs and xenobiotic compounds.
Gene Name:: NNMT
Uniprot ID:: P40261
Molecular weight:: 29573.705

Reactions

S-Adenosylmethionine + Niacinamide → S-Adenosylhomocysteine + 1-Methylnicotinamide	details
S-Adenosylmethionine + Niacinamide + Hydrogen Ion → S-Adenosylhomocysteine + 1-Methylnicotinamide	details

Showing metabocard for 1-Methylnicotinamide (HMDB0000699)

Structure for HMDB0000699 (1-Methylnicotinamide)

Enzymes

Reactions

Reactions