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Niacinamide (YMDB00274)

Identification
YMDB IDYMDB00274
NameNiacinamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionNiacinamide, 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
Thumb
MOLSDFPDBSMILESInChI
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 number98-92-0
WeightAverage: 122.1246
Monoisotopic: 122.048012824
InChI KeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
InChIInChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
IUPAC Namepyridine-3-carboxamide
Traditional IUPAC Namenicotinamide
Chemical FormulaC6H6N2O
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point130 °C
Experimental Properties
PropertyValueReference
Water Solubility500 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
LogP-0.37 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility50.1 g/LALOGPS
logP-0.45ALOGPS
logP-0.39ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)3.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.98 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability11.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • nucleus
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB012485
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
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
NAD + water → hydron + Niacinamide + Adenosine diphosphate ribose
NAD + water ↔ hydron + Niacinamide + Adenosine diphosphate ribose
water + Niacinamide ↔ Nicotinic acid + Ammonium
Niacinamide + S-Adenosylmethionine → 1-Methylnicotinamide + S-Adenosylhomocysteine
phosphate + Nicotinamide riboside ↔ hydron + Niacinamide + Ribose 1-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-0900000000-acb6a21304b0c09c8472JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd538JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9500000000-790385e574240b8d39deJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2910000000-d760b65bb76d6464038eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-4900000000-47c6f72d1bb5465c1376JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-1809e537780b814af0c9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-c4a5ff5285417499eff8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-0e84a60cc2a2d44704f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-acb6a21304b0c09c8472JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd538JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9500000000-790385e574240b8d39deJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2910000000-d760b65bb76d6464038eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-4900000000-47c6f72d1bb5465c1376JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-23a567506bfbc259e77cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-8900000000-931c139355be3ef594f2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-2900000000-72a7c92eb2667f5b6c3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kor-9800000000-89d56b6cb7e033699d24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-eed71abbb10ba926c13dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-3900000000-0c62aa6aba6e23b6c195JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9100000000-4357a8833611d1756c59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-c9685717817d0081fe6dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a78JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f6d71a6c467f84ddd6abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-62c4bd312efbfa37d1a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-05714b528dc84942b9dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-edb6a77c0dfdcbdacc5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-eed71abbb10ba926c13dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-3900000000-0c62aa6aba6e23b6c195JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-4357a8833611d1756c59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-c9685717817d0081fe6dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a78JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-960acce7ead55399b5dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c7ec333d35eb740520aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9600000000-466f98885e2efba73575JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9200000000-6ef8d7e5edcdd0b02758JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-f38177aa475e58941088JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-6a883d82fcd7c450f6ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-882d0c59d946a5087b9fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0kor-9600000000-2b1c5667d92bc1b80b36JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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
  • 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:
ResourceLink
CHEBI ID17154
HMDB IDHMDB01406
Pubchem Compound ID936
Kegg IDC00153
ChemSpider ID911
FOODB IDFDB012485
WikipediaNiacinamide
BioCyc IDNIACINAMIDE

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.