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Identification
YMDB IDYMDB00741
Namenicotinic acid D-ribonucleotide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionnicotinate beta-D-ribonucleotide, also known as b-nicotinic acid D-ribonucleotide, belongs to the class of organic compounds known as purine ribonucleoside polyphosphates. These are purine ribobucleotides with polyphosphate (with 4 or more phosphate) group linked to the ribose moiety. nicotinate beta-D-ribonucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). In yeast, nicotinate beta-D-ribonucleotide is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
Synonyms
  • beta-nicotinate d-ribonucleotide
  • Nicotinate D-ribonucleotide
  • nicotinate ribonucleotide
  • nicotinic acid ribonucleotide
  • b-Nicotinate D-ribonucleotide
  • b-Nicotinic acid D-ribonucleotide
  • beta-Nicotinic acid D-ribonucleotide
  • β-Nicotinate D-ribonucleotide
  • β-Nicotinic acid D-ribonucleotide
  • Nicotinic acid D-ribonucleotide
  • Nicotinate b-D-ribonucleotide
  • Nicotinate β-D-ribonucleotide
  • Nicotinic acid b-D-ribonucleotide
  • Nicotinic acid beta-D-ribonucleotide
  • Nicotinic acid β-D-ribonucleotide
  • Nicotinate mononucleotide
  • Nicotinic acid mononucleotide
  • Deamido nicotinamide ribonucleotide
  • Deamido-NMN
  • Nicotinic acid ribotide
  • Nicotinic mononucleotide
  • beta-Nicotinic acid mononucleotide
  • β-Nicotinic acid mononucleotide
CAS numberNot Available
WeightAverage: 336.2119
Monoisotopic: 336.048442595
InChI KeyJOUIQRNQJGXQDC-ZYUZMQFOSA-O
InChIInChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/p+1/t7-,8-,9-,10-/m1/s1
IUPAC Name3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional IUPAC Name3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium
Chemical FormulaC11H15NO9P
SMILESO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CC=CC(=C1)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nicotinic acid nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinic acid or a derivative thereof.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyridine nucleotides
Sub ClassNicotinic acid nucleotides
Direct ParentNicotinic acid nucleotides
Alternative Parents
Substituents
  • Nicotinic-acid-nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyridine
  • Pyridinium
  • Alkyl phosphate
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP-0.99ALOGPS
logP-5.4ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.2ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area157.63 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.89 m³·mol⁻¹ChemAxon
Polarizability28.66 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
SMPDB Reactions
Adenosine triphosphate + Nicotinate D-ribonucleosideADP + hydron + nicotinic acid D-ribonucleotide
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-9704000000-b4f3d91df4a5fb88cc5eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000b-9221310000-f2425a1cc55147b91d2bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1009000000-227e6a4729b96a705fa4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-5239000000-223d08e3fd97af58d374JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9500000000-db23a80f58b7ac9781fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1009000000-f16974a59d3ff46358d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9001000000-ca67d776dd7d3f5d4650JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5808f9bb378f2d60cd9bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0479000000-61da4c1926ec7950c051JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00si-5950000000-2c01c6fd1632660b38c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9500000000-3dbb0f51364659db892eJSpectraViewer
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
References
References:
  • 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
  • Lu, S. P., Kato, M., Lin, S. J. (2009). "Assimilation of endogenous nicotinamide riboside is essential for calorie restriction-mediated life span extension in Saccharomyces cerevisiae." J Biol Chem 284:17110-17119.19416965
  • Magni, G., Amici, A., Emanuelli, M., Orsomando, G., Raffaelli, N., Ruggieri, S. (2004). "Structure and function of nicotinamide mononucleotide adenylyltransferase." Curr Med Chem 11:873-885.15078171
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15763
HMDB IDHMDB0001132
Pubchem Compound ID121992
Kegg IDC01185
ChemSpider ID24785392
FOODB IDFDB022444
Wikipedia IDNot Available
BioCyc IDNICOTINATE_NUCLEOTIDE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA)
Gene Name:
BNA6
Uniprot ID:
P43619
Molecular weight:
32364.69922
Reactions
Nicotinate D-ribonucleotide + diphosphate + CO(2) → pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN)
Gene Name:
NRK1
Uniprot ID:
P53915
Molecular weight:
27689.30078
Reactions
ATP + N-ribosylnicotinamide → ADP + nicotinamide ribonucleotide.
ATP + D-ribosylnicotinate → ADP + nicotinate D-ribonucleotide.
General function:
Involved in nucleotidyltransferase activity
Specific function:
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+);ATP + nicotinate ribonucleotide = diphosphate + deamido-NAD+
Gene Name:
NMA2
Uniprot ID:
P53204
Molecular weight:
44908.69922
Reactions
ATP + nicotinamide ribonucleotide → diphosphate + NAD(+).
ATP + nicotinate ribonucleotide → diphosphate + deamido-NAD+
General function:
Involved in nucleotidyltransferase activity
Specific function:
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+)
Gene Name:
NMA1
Uniprot ID:
Q06178
Molecular weight:
45858.60156
Reactions
ATP + nicotinamide ribonucleotide → diphosphate + NAD(+).
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.