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Identification
YMDB IDYMDB00224
NameNicotinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionNicotinic acid, also known as niacin or nicotinate, 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 catalyzed by the enzyme nicotinate phosphoribosyltransferase. In addition, nicotinic acid and ammonium can be biosynthesized from niacinamide; which is mediated 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
Thumb
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 number59-67-6
WeightAverage: 123.1094
Monoisotopic: 123.032028409
InChI KeyPVNIIMVLHYAWGP-UHFFFAOYSA-N
InChIInChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
IUPAC Namepyridine-3-carboxylic acid
Traditional IUPAC Nameniacin
Chemical FormulaC6H5NO2
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point236.6 °C
Experimental Properties
PropertyValueReference
Water Solubility18 mg/mL at 20 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP0.36 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility83.1 g/LALOGPS
logP0.29ALOGPS
logP-0.17ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Extracellular, Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
SMPDB Reactions
water + Adenosine triphosphate + Phosphoribosyl pyrophosphate + Nicotinic acidNicotinic acid mononucleotide + Pyrophosphate + ADP + phosphate
Niacinamide + waterNicotinic acid + Ammonium
KEGG Reactions
Nicotinic acid + hydron + Phosphoribosyl pyrophosphatePyrophosphate + Nicotinic acid mononucleotide
water + NiacinamideNicotinic acid + Ammonium
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
2843 ± 0 µM hops, malted barleyanaerobicBaker's yeastAlcoholic 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 barleyanaerobicBaker's yeastAlcoholic 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 juiceanaerobicBaker's yeastAlcoholic 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-053i-0900000000-5daf0093df6c21c7279fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-053i-0900000000-f38b6609b45de8c74565JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0540-0900000000-4f55c81a6cd42f1b961dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-057r-5900000000-00bf3662b5b9db533c0aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0569-2900000000-7820ea736b03b71d2cb8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kmi-7900000000-9e4efda763cce5ddfe57JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-053i-0900000000-5daf0093df6c21c7279fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-053i-0900000000-f38b6609b45de8c74565JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0540-0900000000-4f55c81a6cd42f1b961dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-057r-5900000000-00bf3662b5b9db533c0aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0569-2900000000-7820ea736b03b71d2cb8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0540-0900000000-a701904fe6ded0abd98fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-9700000000-d7620f1dc8f42d1498b9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9600000000-c3303cf4e83870b3e656JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1900000000-27508608b33f1fb9f221JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-9100000000-a2037c9695659dceabd1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-9100000000-4a2649a83ad2a40e5194JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kmi-7900000000-1bc47d1b1850f54fb7c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-1900000000-a352c5ce16d4b682b052JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-ab23ecb032e387b40bd9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-02e37a1cfd3947037579JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-75d7e6658d2d6eca736eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0udi-9000000000-21a2d68d4f364c596f1dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0ab9-0900000000-a74db528f61c435876c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-6900000000-773c08ab92ace4d48a9cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00aj-9100000000-07b12fbe942e6c7fb12dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-005a-9000000000-66e0a5ba2ca8dbba1ed5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-fbf8ba47b56d7cc7be81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0900000000-eaf82f6ab0befde118e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00di-0900000000-eaf82f6ab0befde118e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9300000000-b1a48f694fba565108a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-a352c5ce16d4b682b052JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-ab23ecb032e387b40bd9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-25068c42378f72756922JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-6278a1e122005f48fcafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9000000000-e4e41ed9bef32955889eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4900000000-85d44ecd8ad348eeacd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-4911305982583ae20895JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4dea4a2d4a55907605eaJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0kor-8900000000-7d3f033a49f5fad75f33JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID15940
HMDB IDHMDB01488
Pubchem Compound ID938
Kegg IDC00253
ChemSpider ID913
FOODB IDFDB001014
WikipediaNiacin
BioCyc IDNIACINE

Enzymes

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).
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

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