Showing Compound Nicotinamide (FDB012485)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:12 UTC

Update date

2020-09-17 15:38:55 UTC

Primary ID

FDB012485

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Nicotinamide

Description

Niacinamide, also known as nicotinamid or nicovit, 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. Niacinamide is a strong basic compound (based on its pKa). Niacinamide exists in all living species, ranging from bacteria to humans. niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate through the action of the enzyme nicotinamide phosphoribosyltransferase. In humans, niacinamide is involved in the metabolic disorder called the nad+ signalling pathway (cancer). Niacinamide is an odorless tasting compound. Outside of the human body, Niacinamide is found, on average, in the highest concentration within a few different foods, such as common sages, milk (cow), and cocoa beans and in a lower concentration in common pea and beers. Niacinamide has also been detected, but not quantified in, several different foods, such as pineappple sages, boysenberries, cashew nuts, macadamia nut (m. tetraphylla), and sweet marjorams. This could make niacinamide a potential biomarker for the consumption of these foods. Niacinamide is a potentially toxic compound. A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.

CAS Number

98-92-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-Pyridinecarboxamide	ChEBI
beta-Pyridinecarboxamide	ChEBI
Niacin	ChEBI
Nicotinamid	ChEBI
Nicotinic acid amide	ChEBI
Nicotinsaeureamid	ChEBI
Nikotinamid	ChEBI
Nikotinsaeureamid	ChEBI
Vitamin b3	ChEBI
Vitamin PP	ChEBI
Nicotinamide	Kegg
b-Pyridinecarboxamide	Generator
Β-pyridinecarboxamide	Generator
Nicotinate amide	Generator
3-Carbamoylpyridine	HMDB
3-Pyridinecarboxylic acid amide	HMDB
Acid amide	HMDB
Amid kyseliny nikotinove	HMDB
Amide PP	HMDB
Aminicotin	HMDB
Amixicotyn	HMDB
Amnicotin	HMDB
Austrovit PP	HMDB
Benicot	HMDB
Delonin amide	HMDB
Dipegyl	HMDB
Dipigyl	HMDB
Endobion	HMDB
Factor PP	HMDB
Hansamid	HMDB
Inovitan PP	HMDB
m-(Aminocarbonyl)pyridine	HMDB
Mediatric	HMDB
NAM	HMDB
Nandervit-N	HMDB
Niacevit	HMDB
Niamide	HMDB
Niavit PP	HMDB
Nicamide	HMDB
Nicamina	HMDB
Nicamindon	HMDB
Nicasir	HMDB
Nicobion	HMDB
Nicofort	HMDB
Nicogen	HMDB
Nicomidol	HMDB
Nicosan 2	HMDB
Nicosylamide	HMDB
Nicota	HMDB
Nicotamide	HMDB
Nicotilamide	HMDB
Nicotililamido	HMDB
Nicotinamida	HMDB
Nicotinamidum	HMDB
Nicotine acid amide	HMDB
Nicotine amide	HMDB
Nicotinic amide	HMDB
Nicotinsaureamid	HMDB
Nicotol	HMDB
Nicotylamide	HMDB
Nicotylamidum	HMDB
Nicovel	HMDB
Nicovit	HMDB
Nicovitina	HMDB
Nicovitol	HMDB
Nicozymin	HMDB
Nictoamide	HMDB
Niko-tamin	HMDB
Niocinamide	HMDB
Niozymin	HMDB
Papulex	HMDB
Pelmin	HMDB
Pelmine	HMDB
Pelonin amide	HMDB
PP-Faktor	HMDB
Propamine a	HMDB
Pyridine-3-carboxylic acid amide	HMDB
Savacotyl	HMDB
Vi-nicotyl	HMDB
Vi-noctyl	HMDB
Witamina PP	HMDB
3 Pyridinecarboxamide	HMDB
Astra brand OF niacinamide	HMDB
b 3, Vitamin	HMDB
Niacinamide merck brand	HMDB
Pharmagenix brand OF niacinamide	HMDB
b3, Vitamin	HMDB
Enduramide	HMDB
Jenapharm, nicotinsäureamid	HMDB
Niacinamide jenapharm brand	HMDB
Niacinamide pharmagenix brand	HMDB
Jenapharm brand OF niacinamide	HMDB
Nicotinsäureamid jenapharm	HMDB
Vitamin b 3	HMDB
Merck brand OF niacinamide	HMDB
Niacinamide astra brand	HMDB
Niacinamide	ChEBI
β-Pyridinecarboxamide	biospider
3-(Aminocarbonyl)pyridine	biospider
3-Amidopyridine	biospider
6-Aminonicotinamide	biospider
Vitamin B3 (Nicotinamide)	biospider
Vitamin PP (Nicotinamide)	biospider
β-pyridinecarboxamide	Generator

Predicted Properties

Property	Value	Source
Water Solubility	50.1 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.39	ChemAxon
logS	-0.39	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	3.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.98 m³·mol⁻¹	ChemAxon
Polarizability	11.71 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

Chemical Formula

C6H6N2O

IUPAC name

pyridine-3-carboxamide

InChI Identifier

InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

InChI Key

DFPAKSUCGFBDDF-UHFFFAOYSA-N

Isomeric SMILES

NC(=O)C1=CC=CN=C1

Average Molecular Weight

122.1246

Monoisotopic Molecular Weight

122.048012824

Classification

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
Primary 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

pyridine alkaloid (CHEBI:17154 )
pyridinecarboxamide (CHEBI:17154 )
Water-soluble vitamins (C00153 )
Pyridine alkaloids (C00153 )
a vitamin (NIACINAMIDE )
an aliphatic amide (NIACINAMIDE )

Ontology

Dermal

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Organ and components:

Tissue and substructures:

Cell and elements:

Extracellular

Cell:

Biofluid and excreta:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 59.01%; H 4.95%; N 22.94%; O 13.10%	DFC
Melting Point	Mp 129-130°	DFC
Boiling Point	Bp0.0005 150-160°	DFC
Experimental Water Solubility	500 mg/mL at 25 oC	MERCK INDEX (1996)
Experimental logP	-0.37	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 3.33 (20°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0kor-9600000000-2b1c5667d92bc1b80b36	2014-09-20	View Spectrum
GC-MS	Nicotinamide, 1 TMS, GC-MS Spectrum	splash10-004i-0900000000-acb6a21304b0c09c8472	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004r-0900000000-ce86dcff0153b66dd538	Spectrum
GC-MS	Nicotinamide, 1 TMS, GC-MS Spectrum	splash10-004i-9500000000-790385e574240b8d39de	Spectrum
GC-MS	Nicotinamide, 2 TMS, GC-MS Spectrum	splash10-0udi-2910000000-d760b65bb76d6464038e	Spectrum
GC-MS	Nicotinamide, 1 TMS, GC-MS Spectrum	splash10-004i-4900000000-47c6f72d1bb5465c1376	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-0kor-9800000000-1809e537780b814af0c9	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-0kor-9800000000-c4a5ff5285417499eff8	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-0e84a60cc2a2d44704f4	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-acb6a21304b0c09c8472	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004r-0900000000-ce86dcff0153b66dd538	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004i-9500000000-790385e574240b8d39de	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-0udi-2910000000-d760b65bb76d6464038e	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-47c6f72d1bb5465c1376	Spectrum
GC-MS	Nicotinamide, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-23a567506bfbc259e77c	Spectrum
Predicted GC-MS	Nicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-8900000000-931c139355be3ef594f2	Spectrum
Predicted GC-MS	Nicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-2900000000-72a7c92eb2667f5b6c3f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kor-9800000000-89d56b6cb7e033699d24	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-eed71abbb10ba926c13d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9100000000-4357a8833611d1756c59	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-c9685717817d0081fe6d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-f6d71a6c467f84ddd6ab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-62c4bd312efbfa37d1a1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-05714b528dc84942b9db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-edb6a77c0dfdcbdacc5d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-eed71abbb10ba926c13d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-4357a8833611d1756c59	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-c9685717817d0081fe6d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0900000000-960acce7ead55399b5db	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2c7ec333d35eb740520a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-9600000000-466f98885e2efba73575	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9200000000-6ef8d7e5edcdd0b02758	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-f38177aa475e58941088	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-9800000000-6a883d82fcd7c450f6ce	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-882d0c59d946a5087b9f	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17154

Phenol-Explorer ID

Not Available

DrugBank ID

DB02701

HMDB ID

HMDB01406

CRC / DFC (Dictionary of Food Compounds) ID

HHJ27-Z:HHJ27-Z

EAFUS ID

2662

Dr. Duke ID

NICOTINIC-ACID-AMIDE|NICOTINAMIDE

BIGG ID

34058

KNApSAcK ID

C00000209

HET ID

NCA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1068911

SuperScent ID

Not Available

Wikipedia ID

Niacinamide

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
depressant			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Purine nucleoside phosphorylase	PNP	P00491

Pathways

Name	SMPDB Link	KEGG Link
Nicotinate and Nicotinamide Metabolism	SMP00048	map00760

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).