Bovine Metabolome Database: Showing metabocard for 1-Methylnicotinamide (BMDB0000699)

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

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:07 UTC

Update Date

2020-05-21 16:28:55 UTC

BMDB ID

BMDB0000699

Secondary Accession Numbers

BMDB00699

Metabolite Identification

Common Name

1-Methylnicotinamide

Description

1-Methylnicotinamide, also known as 1-methylnicotinamide or 1-methylnicotinamide, 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 is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylnicotinamide exists in all living species, ranging from bacteria to humans. 1-Methylnicotinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and 1-methylnicotinamide can be biosynthesized from S-adenosylmethionine and niacinamide; which is catalyzed by the enzyme nicotinamide N-methyltransferase. In addition, 1-Methylnicotinamide can be converted into N1-methyl-2-pyridone-5-carboxamide through the action of the enzyme aldehyde oxidase. In cattle, 1-methylnicotinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.

Structure

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

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

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

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
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	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-5527bd16347dfbb8af1b	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Nicotinate and Nicotinamide Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

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

Not Available

Enzymes

Enzyme Details

1. Phenylethanolamine N-methyltransferase

General function:: Involved in phenylethanolamine N-methyltransferase acti
Specific function:: Converts noradrenaline to adrenaline.
Gene Name:: PNMT
Uniprot ID:: P10938
Molecular weight:: 30918.0

Reactions

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

Enzyme Details

2. Aldehyde oxidase 1

General function:: Nucleotide transport and metabolism
Specific function:: Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:: AOX1
Uniprot ID:: P48034
Molecular weight:: 147611.0

Reactions

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

Showing metabocard for 1-Methylnicotinamide (BMDB0000699)

Structure for BMDB0000699 (1-Methylnicotinamide)

Enzymes

Reactions

Reactions