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Identification
YMDB IDYMDB00224
NameNicotinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionNicotinic 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
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