Nicotinic acid (YMDB00224)

Identification

YMDB ID

YMDB00224

Name

Nicotinic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Nicotinic acid, also known as niacin or 3-carboxypyridine, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Nicotinic acid is a strong basic compound (based on its pKa). Nicotinic acid exists in all living species, ranging from bacteria to humans. Within yeast, nicotinic acid participates in a number of enzymatic reactions. In particular, phosphoribosyl pyrophosphate and nicotinic acid can be converted into nicotinic acid mononucleotide; which is mediated by the enzyme nicotinate phosphoribosyltransferase. In addition, nicotinic acid and ammonium can be biosynthesized from niacinamide; which is catalyzed by the enzyme nicotinamidase. In yeast, nicotinic acid is involved in the metabolic pathway called the nad metabolism pathway. Nicotinic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

3-Carboxylpyridine
3-Carboxypyridine
3-Pyridinecarboxylate
3-Pyridinecarboxylic acid
3-Pyridylcarboxylate
3-Pyridylcarboxylic acid
Akotin
anti-Pellagra vitamin
Apelagrin
b-Pyridinecarboxylic acid
Daskil
Davitamon PP
Diacin
Direktan
Efacin
Enduracin
Kyselina nikotinova
Linic
M-Pyridinecarboxylic Acid
NAH
Naotin
Niac
niacin
niacine
Niacor
Nicacid
nicamin
Nicangin
NICO
Nico-Span
nicobid
nicocap
Nicocidin
Nicocrisina
Nicodan
Nicodelmine
Nicodon
nicolar
Niconacid
Niconat
Niconazid
Nicorol
Nicosan 3
Nicoside
Nicosyl
Nicotamin
Nicotene
Nicotil
Nicotinate
Nicotine Acid
Nicotinic acid
Nicotinipca
Nicotinsaure
Nicovasan
Nicovasen
Nicovel
Nicyl
Nipellen
Nyclin
Pellagramin
Pellagrin
Pelonin
Peviton
Pyridine-3-carbonic acid
Pyridine-3-carboxylic acid
Pyridine-beta-carboxylic acid
Pyridine-carboxylique-3
Pyridinecarboxylic Acid
Pyridylcarboxylic Acid
SK-Niacin
Slo-niacin
Tega-Span
Tinic
Vitamin B
Vitamin B3
Vitaplex N
wampocap
Acide nicotinique
Acido nicotinico
Acidum nicotinicum
beta-Pyridinecarboxylic acid
Nikotinsaeure
P.P. factor
Pellagra preventive factor
PP Factor
Niaspan
b-Pyridinecarboxylate
beta-Pyridinecarboxylate
Β-pyridinecarboxylate
Β-pyridinecarboxylic acid
m-Pyridinecarboxylate
Pyridine-b-carboxylate
Pyridine-b-carboxylic acid
Pyridine-beta-carboxylate
Pyridine-β-carboxylate
Pyridine-β-carboxylic acid
Aluminum salt, niacin
Induracin
Niacin cobalt (2+) salt
Niacin iron (2+) salt
Niacin lithium salt
Niacin magnesium salt
Niacin sodium salt
Nico-400
Potassium salt, niacin
Sodium salt, niacin
Tosylate, niacin
Nicotinate, lithium
Hydrochloride, niacin
Niacin aluminum salt
Niacin calcium salt
Niacin copper (2+) salt
Niacin hydrochloride
Niacin lithium salt, hemihydrate
Nico400
Tartrate, niacin
3 Pyridinecarboxylic acid
Lithium nicotinate
Niacin ammonium salt
Niacin manganese (2+) salt
Niacin potassium salt
Niacin tartrate
Niacin tosylate
Niacin zinc salt
Nico 400

CAS number

59-67-6

Weight

Average: 123.1094
Monoisotopic: 123.032028409

InChI Key

PVNIIMVLHYAWGP-UHFFFAOYSA-N

InChI

InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

IUPAC Name

pyridine-3-carboxylic acid

Traditional IUPAC Name

niacin

Chemical Formula

C₆H₅NO₂

SMILES

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
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:15940 )
pyridinemonocarboxylic acid (CHEBI:15940 )
Water-soluble vitamins (C00253 )
Pyridine alkaloids (C00253 )

Physical Properties

State

Solid

Charge

Melting point

236.6 °C

Experimental Properties

Property	Value	Reference
Water Solubility	18 mg/mL at 20 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	0.36 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	83.1 g/L	ALOGPS
logP	0.29	ALOGPS
logP	-0.17	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	4.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	11.3 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

Cytoplasm, Extracellular, Mitochondrion

Organoleptic Properties

Not Available

SMPDB Pathways

NAD metabolism

PW002421

KEGG Pathways

Nicotinate and nicotinamide metabolism

ec00760

SMPDB Reactions

water + Adenosine triphosphate + Phosphoribosyl pyrophosphate + Nicotinic acid → Nicotinic acid mononucleotide + Pyrophosphate + ADP + phosphate

Niacinamide + water → Nicotinic acid + Ammonium

KEGG Reactions

Nicotinic acid + hydron + Phosphoribosyl pyrophosphate → Pyrophosphate + Nicotinic acid mononucleotide

water + Niacinamide ↔ Nicotinic acid + Ammonium

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
2843 ± 0 µM	hops, malted barley	anaerobic	Baker's yeast	Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
42 ± 2 µM	hops, malted barley	anaerobic	Baker's yeast	Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
18 ± 0 µM	grape juice	anaerobic	Baker's yeast	Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here

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)	splash10-053i-0900000000-5daf0093df6c21c7279f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-053i-0900000000-f38b6609b45de8c74565	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0540-0900000000-4f55c81a6cd42f1b961d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-057r-5900000000-00bf3662b5b9db533c0a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0569-2900000000-7820ea736b03b71d2cb8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kmi-7900000000-9e4efda763cce5ddfe57	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-053i-0900000000-5daf0093df6c21c7279f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-053i-0900000000-f38b6609b45de8c74565	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-4f55c81a6cd42f1b961d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-057r-5900000000-00bf3662b5b9db533c0a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0569-2900000000-7820ea736b03b71d2cb8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-a701904fe6ded0abd98f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-9700000000-d7620f1dc8f42d1498b9	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9600000000-c3303cf4e83870b3e656	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-1900000000-27508608b33f1fb9f221	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9100000000-a2037c9695659dceabd1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ufr-9100000000-4a2649a83ad2a40e5194	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kmi-7900000000-1bc47d1b1850f54fb7c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-1900000000-a352c5ce16d4b682b052	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-02e37a1cfd3947037579	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-75d7e6658d2d6eca736e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-21a2d68d4f364c596f1d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0ab9-0900000000-a74db528f61c435876c8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-6900000000-773c08ab92ace4d48a9c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00aj-9100000000-07b12fbe942e6c7fb12d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-005a-9000000000-66e0a5ba2ca8dbba1ed5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-fbf8ba47b56d7cc7be81	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9300000000-b1a48f694fba565108a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-1900000000-a352c5ce16d4b682b052	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-25068c42378f72756922	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3900000000-6278a1e122005f48fcaf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9000000000-e4e41ed9bef32955889e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-4900000000-85d44ecd8ad348eeacd1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-4911305982583ae20895	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4dea4a2d4a55907605ea	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0kor-8900000000-7d3f033a49f5fad75f33	JSpectraViewer \| MoNA
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	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
Belenky, P., Christensen, K. C., Gazzaniga, F., Pletnev, A. A., Brenner, C. (2009). "Nicotinamide riboside and nicotinic acid riboside salvage in fungi and mammals. Quantitative basis for Urh1 and purine nucleoside phosphorylase function in NAD+ metabolism." J Biol Chem 284:158-164.19001417
de Figueiredo, L. F., Gossmann, T. I., Ziegler, M., Schuster, S. (2011). "Pathway Analysis of NAD+ metabolism." Biochem J :.21729004
Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page

Synthesis Reference:

McElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.

External Links:

Resource	Link
CHEBI ID	15940
HMDB ID	HMDB01488
Pubchem Compound ID	938
Kegg ID	C00253
ChemSpider ID	913
FOODB ID	FDB001014
Wikipedia	Niacin
BioCyc ID	NIACINE

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. Nicotinate phosphoribosyltransferase

General function:: Involved in nicotinate phosphoribosyltransferase activity
Specific function:: Essential for growth under anaerobic conditions
Gene Name:: NPT1
Uniprot ID:: P39683
Molecular weight:: 49018.19922

Reactions

Nicotinate D-ribonucleotide + diphosphate → nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate.

Transporters

Protein Details

1. High-affinity nicotinic acid transporter

General function:: Involved in transmembrane transport
Specific function:: Involved in the uptake of nicotinic acid
Gene Name:: TNA1
Uniprot ID:: P53322
Molecular weight:: 60134.30078

Structure for #<Compound:0xa72157bc>

Enzymes

Reactions

Reactions

Transporters