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Identification
YMDB IDYMDB00193
NameNicotinic acid mononucleotide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionNicotinic acid mononucleotide, also known as beta-nicotinate D-ribonucleotide or deamido-NMN, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Nicotinic acid mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinic acid mononucleotide exists in all eukaryotes, ranging from yeast to humans. Within yeast, nicotinic acid mononucleotide participates in a number of enzymatic reactions. In particular, nicotinic acid mononucleotide can be biosynthesized from quinolinic acid and phosphoribosyl pyrophosphate through its interaction with the enzyme nicotinate-nucleotide pyrophosphorylase [carboxylating]. In addition, nicotinic acid mononucleotide can be converted into nicotinic acid adenine dinucleotide through the action of the enzyme nicotinamide/nicotinic acid mononucleotide adenylyltransferase. In yeast, nicotinic acid mononucleotide is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
Synonyms
  • 3-carboxy-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt
  • 3-carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)-Pyridinium inner salt
  • 3-carboxy-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt
  • 3-Carboxy-1-beta-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
  • 3-Carboxy-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
  • 3-Pyridinecarboxylic acid mononucleotide
  • Beta-nicotinate D-ribonucleotide
  • beta-Nicotinic acid mononucleotide
  • Deamido nicotinamide ribonucleotide
  • deamido-nicotinamide mononucleotide
  • Deamido-NMN
  • NaMN
  • Nicotinate D-ribonucleoside
  • Nicotinate D-ribonucleotide
  • Nicotinate mononucleotide
  • nicotinate nucleotide
  • nicotinate ribonucleotide
  • nicotinate-D-ribonucleotide
  • nicotinate-delta-ribonucleotide
  • Nicotinic acid mononucleotide
  • Nicotinic acid ribonucleotide
  • Nicotinic acid ribotide
  • Nicotinic mononucleotide
CAS number321-02-8
WeightAverage: 337.2198
Monoisotopic: 337.056267627
InChI KeyOGCWVIVNTBZPBW-BHRXDNSCSA-N
InChIInChI=1S/C11H16NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-3,6-10,13-14H,4-5H2,(H2-,15,16,17,18,19)/t6?,7-,8-,9-,10-/m1/s1
IUPAC Name3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium
Traditional IUPAC Name3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium
Chemical FormulaC11H16NO9P
SMILES[H]OC(=O)C1([H])C([H])=C([H])C([H])=[N+](C1([H])[H])[C@]1([H])O[C@]([H])(C([H])([H])OP([O-])(=O)O[H])[C@@]([H])(O[H])[C@@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic zwitterion
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.83 g/LALOGPS
logP0.18ALOGPS
logP-5.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area159.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.91 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
SMPDB Reactions
Quinolinic acid + hydron + Phosphoribosyl pyrophosphatePyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
Nicotinic acid mononucleotide + hydron + Adenosine triphosphatedeamido-NAD(+) + Pyrophosphate
water + Adenosine triphosphate + Phosphoribosyl pyrophosphate + Nicotinic acidNicotinic acid mononucleotide + Pyrophosphate + ADP + phosphate
KEGG Reactions
Nicotinic acid + hydron + Phosphoribosyl pyrophosphatePyrophosphate + Nicotinic acid mononucleotide
Adenosine triphosphate + hydron + Nicotinic acid mononucleotidePyrophosphate + deamido-NAD(+)
Quinolinic acid + Phosphoribosyl pyrophosphate + hydronPyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • de Figueiredo, L. F., Gossmann, T. I., Ziegler, M., Schuster, S. (2011). "Pathway Analysis of NAD+ metabolism." Biochem J :.21729004
  • Lu, S. P., Lin, S. J. (2011). "Phosphate-responsive signaling pathway is a novel component of NAD+ metabolism in Saccharomyces cerevisiae." J Biol Chem 286:14271-14281.21349851
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15763
HMDB IDHMDB01132
Pubchem Compound ID121991
Kegg IDC01185
ChemSpider IDNot Available
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.