Niacinamide (YMDB00274)

Identification

YMDB ID

YMDB00274

Name

Niacinamide

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

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. Within yeast, niacinamide participates in a number of enzymatic reactions. In particular, niacinamide can be converted into nicotinic acid and ammonium; which is mediated by the enzyme nicotinamidase. In addition, D-ribose and niacinamide can be biosynthesized from nicotinamide riboside; which is mediated by the enzyme uridine nucleosidase. In yeast, niacinamide is involved in the metabolic pathway called the nad metabolism pathway. Niacinamide is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

98-92-0

Weight

Average: 122.1246
Monoisotopic: 122.048012824

InChI Key

DFPAKSUCGFBDDF-UHFFFAOYSA-N

InChI

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

IUPAC Name

pyridine-3-carboxamide

Traditional IUPAC Name

nicotinamide

Chemical Formula

C₆H₆N₂O

SMILES

[H]N([H])C(=O)C1=C([H])N=C([H])C([H])=C1[H]

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
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 )

Physical Properties

State

Solid

Charge

Melting point

130 °C

Experimental Properties

Property	Value	Reference
Water Solubility	500 mg/mL at 25 oC [MERCK INDEX (1996)]	PhysProp
LogP	-0.37 [HANSCH,C ET AL. (1995)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
nucleus
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Odorless	FDB012485

SMPDB Pathways

NAD metabolism

PW002421

KEGG Pathways

Nicotinate and nicotinamide metabolism

ec00760

SMPDB Reactions

Niacinamide + water → Nicotinic acid + Ammonium

Nicotinamide riboside + water → hydron + D-Ribose + Niacinamide

NAD + water + [histone]-N6-acetyl-L-lysine → 3''-O-acetyl-ADP-ribose + a [histone]-L-lysine + Niacinamide

KEGG Reactions

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-0900000000-acb6a21304b0c09c8472	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004r-0900000000-ce86dcff0153b66dd538	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-9500000000-790385e574240b8d39de	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-2910000000-d760b65bb76d6464038e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-4900000000-47c6f72d1bb5465c1376	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kor-9800000000-1809e537780b814af0c9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kor-9800000000-c4a5ff5285417499eff8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-0e84a60cc2a2d44704f4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-acb6a21304b0c09c8472	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004r-0900000000-ce86dcff0153b66dd538	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-9500000000-790385e574240b8d39de	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-2910000000-d760b65bb76d6464038e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-4900000000-47c6f72d1bb5465c1376	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-23a567506bfbc259e77c	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-8900000000-931c139355be3ef594f2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-2900000000-72a7c92eb2667f5b6c3f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kor-9800000000-89d56b6cb7e033699d24	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-eed71abbb10ba926c13d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9100000000-4357a8833611d1756c59	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-c9685717817d0081fe6d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-f6d71a6c467f84ddd6ab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-62c4bd312efbfa37d1a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-05714b528dc84942b9db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-edb6a77c0dfdcbdacc5d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-eed71abbb10ba926c13d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-4357a8833611d1756c59	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-c9685717817d0081fe6d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0900000000-960acce7ead55399b5db	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2c7ec333d35eb740520a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-9600000000-466f98885e2efba73575	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9200000000-6ef8d7e5edcdd0b02758	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-f38177aa475e58941088	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-9800000000-6a883d82fcd7c450f6ce	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-882d0c59d946a5087b9f	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0kor-9600000000-2b1c5667d92bc1b80b36	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Anderson, R. M., Bitterman, K. J., Wood, J. G., Medvedik, O., Sinclair, D. A. (2003). "Nicotinamide and PNC1 govern lifespan extension by calorie restriction in Saccharomyces cerevisiae." Nature 423:181-185.12736687
Belenky, P., Racette, F. G., Bogan, K. L., McClure, J. M., Smith, J. S., Brenner, C. (2007). "Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+." Cell 129:473-484.17482543
Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834

Synthesis Reference:

Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.

External Links:

Resource	Link
CHEBI ID	17154
HMDB ID	HMDB01406
Pubchem Compound ID	936
Kegg ID	C00153
ChemSpider ID	911
FOODB ID	FDB012485
Wikipedia	Niacinamide
BioCyc ID	NIACINAMIDE

Enzymes

Protein Details

1. Nicotinamidase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the deamidation of nicotinamide, an early step in the NAD(+) salvage pathway. Positively regulates SIR2-mediated silencing and longevity by preventing the accumulation of intracellular nicotinamide, an inhibitor of SIR2, during times of stress. Acts also on nicotinyl hydroxamate
Gene Name:: PNC1
Uniprot ID:: P53184
Molecular weight:: 24993.19922

Reactions

Nicotinamide + H(2)O → nicotinate + NH(3).

Protein Details

2. tRNA 2'-phosphotransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: Catalyzes the last step of tRNA splicing, the transfer of the splice junction 2'-phosphate from ligated tRNA to NAD to produce ADP-ribose 1''-2'' cyclic phosphate
Gene Name:: TPT1
Uniprot ID:: Q12272
Molecular weight:: 26196.19922

Reactions

2'-phospho-[ligated tRNA] + NAD(+) → mature tRNA + ADP ribose 1'',2''-phosphate + nicotinamide + H(2)O.

Protein Details

3. Putative nicotinamide N-methyltransferase

General function:: Involved in nicotinamide N-methyltransferase activity
Specific function:: Putative nicotinamide N-methyltransferase involved in rDNA silencing and in lifespan determination
Gene Name:: NNT1
Uniprot ID:: Q05874
Molecular weight:: 29632.30078

Reactions

S-adenosyl-L-methionine + nicotinamide → S-adenosyl-L-homocysteine + 1-methylnicotinamide.

Protein Details

4. Uridine nucleosidase

General function:: Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:: Also acts on cytidine
Gene Name:: URH1
Uniprot ID:: Q04179
Molecular weight:: 37960.0

Reactions

Uridine + H(2)O → D-ribose + uracil.

Structure for #<Compound:0xa73602ac>

Enzymes

Reactions

Reactions

Reactions

Reactions