MiMeDB: Showing metabocard for 1-Methylnicotinamide (MMDBc0000363)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:10 UTC

Update Date

2024-10-15 16:32:37 UTC

Metabolite ID

MMDBc0000363

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

Synonyms

Value	Source
1-Methyl nicotinamide	ChEBI
1-Methylnicotinamide cation	ChEBI
3-(Aminocarbonyl)-1-methylpyridinium	ChEBI
3-Carbamoyl-1-methylpyridin-1-ium	ChEBI
N(1)-Methylnicotinamide	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-Methyl-3-carbamidopyridinium	HMDB
N-Methyl-3-carbamoylpyridinium ion	HMDB
N1-Methylnicotinamide	HMDB
N(1)-Methylnicotinamide chloride	HMDB
N(1)-Methylnicotinamide cyanide	HMDB
N(1)-Methylnicotinamide fluoride	HMDB
N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeled	HMDB
N(1)-Methylnicotinamide methylsulfate	HMDB
N(1)-Methylnicotinamide perchlorate	HMDB
N(1)-Methylnicotinamide bromide	HMDB
N(1)-Methylnicotinamide iodide	HMDB
N(1)-Methylnicotinamide tetrafluoroborate (1-)	HMDB
Trigonellamide chloride	HMDB

Molecular Formula

C₇H₉N₂O

Average Mass

137.1592

Monoisotopic Mass

137.07148792

IUPAC Name

3-carbamoyl-1-methylpyridin-1-ium

Traditional Name

1-methylnicotinamide

CAS Registry Number

Not Available

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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)	-1.5	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5900000000-5a5fd45836c387d92371	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-c99e0e70357eb6fa74bb	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-93675f2b9efbaba4d471	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fvl-9000000000-b1e908db583e418c2545	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-0900000000-9c3104d60f21f6375b0c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-e500f262d42edb9b3ad7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9200000000-496b2cf62a07bea4f746	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-002f-9000000000-a17b3a63979577f6fa9e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00ou-9000000000-46a856cd097a7a14dc90	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000l-6900000000-360fb882a925f7e9edc9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0006-9000000000-babd4e89db309a5c74cf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-9c3104d60f21f6375b0c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-e500f262d42edb9b3ad7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9200000000-052c844f974abba065eb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002f-9000000000-a17b3a63979577f6fa9e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00ou-9000000000-2fe6c195129f32a62a3c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000l-6900000000-360fb882a925f7e9edc9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9000000000-babd4e89db309a5c74cf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0900000000-08a578fa81c8d41a4fe6	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-d889aade6d1014ffb393	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-1900000000-8052aba6067c868e594f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9500000000-579bc8310420ec3d8786	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-141e3a418b748abf9e1d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-33499eeb5abff5a8b53b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e45f804a013c97310f00	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-5527bd16347dfbb8af1b	2021-09-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191797	Aldehyde oxidase	Unknown	Q06278	Homo sapiens
MMDBp0192089	Nicotinamide N-methyltransferase	Unknown	P40261	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001768	S-Adenosylmethionine	1-Methylnicotinamide	nicotinamide N-methyltransferase	VMH; KEGG	30371894
MMDBr0010581	1-Methylnicotinamide	Hydrogen peroxide	aldehyde oxidase 1	VMH; KEGG	30371894
MMDBr0010582	1-Methylnicotinamide	Hydrogen peroxide	aldehyde oxidase 1	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cirrhosis	Slight Increase	Association	Human Blood	HMDB	2142586
Lung cancer	Slight Decrease	Association	Human Urine	HMDB	22157537
Pellagra	Increased	Association	Human Urine	HMDB	17709435
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified			0.099	0.851	uM	Adult (>18 years old)	Both	Cirrhosis	HMDB	2142586
Human Urine	Detected and Quantified	3.0		0.0	14.0	umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	HMDB	22157537
Human Urine	Detected and Quantified	37.00		11.5	62.7	umol/mmol creatinine	Adult (>18 years old)	Both	Pellagra	HMDB	17709435
Human Blood	Detected and Quantified	0.430		0.007	0.850	uM	Adult (>18 years old)	Both	Normal	HMDB	11199218
Human Urine	Detected and Quantified	2.5		2.1	2.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17709435
Human Urine	Detected and Quantified	5.8		1.2	15.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	6.105		0.240	12.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	11199218
Human Urine	Detected and Quantified	7.426	3.509			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	7.749	7.16			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.82		0.26	2.3	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.9		0.67	5.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	3.5		1.3	6.0	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	4.8		1.86	13.94	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000699

DrugBank ID

DB11710

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16797

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Pelletier O, Brassard R: Automated and manual determination of N1-methylnicotinamide in urine. Am J Clin Nutr. 1977 Dec;30(12):2108-16. doi: 10.1093/ajcn/30.12.2108. [PubMed:145178 ]
Carter EG: Quantitation of urinary niacin metabolites by reversed-phase liquid chromatography. Am J Clin Nutr. 1982 Nov;36(5):926-30. doi: 10.1093/ajcn/36.5.926. [PubMed:6215856 ]
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. doi: 10.1093/ajcn/33.10.2157. [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. doi: 10.1016/s0731-7085(00)00425-8. [PubMed:11199218 ]
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. doi: 10.1023/a:1014445329756. [PubMed:11952169 ]
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. doi: 10.1016/s1570-0232(03)00277-0. [PubMed:12829005 ]
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. doi: 10.1111/j.1365-2230.2005.01908.x. [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. doi: 10.1038/sj.bjp.0707383. Epub 2007 Jul 16. [PubMed:17641676 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 1-Methylnicotinamide (MMDBc0000363)

MOL for #<Metabolite:0x0000559d0541b3e0>

3D MOL for #<Metabolite:0x0000559d0541b3e0>

3D SDF for #<Metabolite:0x0000559d0541b3e0>

3D-SDF for #<Metabolite:0x0000559d0541b3e0>

PDB for #<Metabolite:0x0000559d0541b3e0>

3D PDB for #<Metabolite:0x0000559d0541b3e0>

SMILES for #<Metabolite:0x0000559d0541b3e0>

INCHI for #<Metabolite:0x0000559d0541b3e0>

Structure for #<Metabolite:0x0000559d0541b3e0>

3D Structure for #<Metabolite:0x0000559d0541b3e0>