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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:56:01 UTC

HMDB ID

HMDB0000699

Secondary Accession Numbers

HMDB00699

Metabolite Identification

Common Name

1-Methylnicotinamide

Description

1-Methylnicotinamide, also known as trigonellinamide or trigonellamide chloride, 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. 1-Methylnicotinamide exists in all living species, ranging from bacteria to plants to humans. 1-Methylnicotinamide 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 1-methylnicotinamide a potential biomarker for the consumption of these foods. 1-Methylnicotinamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 1-Methylnicotinamide.

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-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

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

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

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	130.425	31661259
DarkChem	[M-H]-	127.388	31661259
AllCCS	[M+H]+	126.644	32859911
AllCCS	[M-H]-	127.847	32859911
DeepCCS	[M+H]+	131.303	30932474
DeepCCS	[M-H]-	129.079	30932474
DeepCCS	[M-2H]-	164.576	30932474
DeepCCS	[M+Na]+	138.915	30932474
AllCCS	[M+H]+	126.6	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.3	32859911
AllCCS	[M-H]-	127.8	32859911
AllCCS	[M+Na-2H]-	129.6	32859911
AllCCS	[M+HCOO]-	131.5	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.	1.56 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2455 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	93.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1003.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	305.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	240.0 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	280.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	241.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	669.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.4 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	817.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	506.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.6 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	140.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methylnicotinamide	C[N+]1=CC=CC(=C1)C(N)=O	2541.3	Standard polar	33892256
1-Methylnicotinamide	C[N+]1=CC=CC(=C1)C(N)=O	1387.0	Standard non polar	33892256
1-Methylnicotinamide	C[N+]1=CC=CC(=C1)C(N)=O	1453.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methylnicotinamide,1TMS,isomer #1	C[N+]1=CC=CC(C(=O)N[Si](C)(C)C)=C1	1541.7	Semi standard non polar	33892256
1-Methylnicotinamide,1TMS,isomer #1	C[N+]1=CC=CC(C(=O)N[Si](C)(C)C)=C1	1547.6	Standard non polar	33892256
1-Methylnicotinamide,1TMS,isomer #1	C[N+]1=CC=CC(C(=O)N[Si](C)(C)C)=C1	1759.0	Standard polar	33892256
1-Methylnicotinamide,2TMS,isomer #1	C[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1572.1	Semi standard non polar	33892256
1-Methylnicotinamide,2TMS,isomer #1	C[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1601.0	Standard non polar	33892256
1-Methylnicotinamide,2TMS,isomer #1	C[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1745.5	Standard polar	33892256
1-Methylnicotinamide,1TBDMS,isomer #1	C[N+]1=CC=CC(C(=O)N[Si](C)(C)C(C)(C)C)=C1	1760.1	Semi standard non polar	33892256
1-Methylnicotinamide,1TBDMS,isomer #1	C[N+]1=CC=CC(C(=O)N[Si](C)(C)C(C)(C)C)=C1	1716.8	Standard non polar	33892256
1-Methylnicotinamide,1TBDMS,isomer #1	C[N+]1=CC=CC(C(=O)N[Si](C)(C)C(C)(C)C)=C1	1918.1	Standard polar	33892256
1-Methylnicotinamide,2TBDMS,isomer #1	C[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2019.6	Semi standard non polar	33892256
1-Methylnicotinamide,2TBDMS,isomer #1	C[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2000.8	Standard non polar	33892256
1-Methylnicotinamide,2TBDMS,isomer #1	C[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	1983.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Nicotinate and nicotinamide metabolism	Not Available

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	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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	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	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
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	7.749 +/- 7.16 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	61.37 (40.64-92.98) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	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	3.0 (0.0-14.0) umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	22157537	details
Urine	Detected and Quantified	37.00 (11.5-62.7) umol/mmol creatinine	Adult (>18 years old)	Both	Pellagra	17709435	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	21389975	details
Urine	Detected and Quantified	7.426 +/- 3.509 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

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 ]
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 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

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

External Links

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

VMH ID

1MNCAM

MarkerDB ID

MDB00000225

Good Scents ID

Not Available

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 ]
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 ]

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 → Nudifloramide + 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)

MOL for HMDB0000699 (1-Methylnicotinamide)

3D MOL for HMDB0000699 (1-Methylnicotinamide)

3D SDF for HMDB0000699 (1-Methylnicotinamide)

3D-SDF for HMDB0000699 (1-Methylnicotinamide)

PDB for HMDB0000699 (1-Methylnicotinamide)

3D PDB for HMDB0000699 (1-Methylnicotinamide)

SMILES for HMDB0000699 (1-Methylnicotinamide)

INCHI for HMDB0000699 (1-Methylnicotinamide)

Structure for HMDB0000699 (1-Methylnicotinamide)

3D Structure for HMDB0000699 (1-Methylnicotinamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions