Record Information
Version1.0
Creation Date2016-09-30 22:41:32 UTC
Update Date2020-05-21 16:28:55 UTC
BMDB IDBMDB0001132
Secondary Accession Numbers
  • BMDB01132
Metabolite Identification
Common NameNicotinic acid mononucleotide
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 possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinic acid mononucleotide exists in all eukaryotes, ranging from yeast to humans. Nicotinic acid mononucleotide participates in a number of enzymatic reactions, within cattle. In particular, Nicotinic acid mononucleotide can be biosynthesized from nicotinate D-ribonucleoside through the action of the enzyme nicotinamide riboside kinase 1. In addition, Nicotinic acid mononucleotide can be converted into nicotinate D-ribonucleoside; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. In cattle, nicotinic acid mononucleotide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
Nicotinate mononucleotideGenerator
3-Carboxy-1-(5-O-phosphono-b-D-ribofuranosyl)-pyridinium inner saltHMDB
3-Carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)-pyridinium inner saltHMDB
3-Carboxy-1-(5-O-phosphono-beta-delta-ribofuranosyl)-pyridinium inner saltHMDB
3-Carboxy-1-beta-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner saltHMDB
3-Carboxy-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner saltHMDB
3-Pyridinecarboxylic acid mononucleotideHMDB
beta-Nicotinate D-ribonucleotideHMDB
beta-Nicotinic acid mononucleotideHMDB
Deamido nicotinamide ribonucleotideHMDB
Deamido-nicotinamide mononucleotideHMDB
Deamido-NMNHMDB
NaMNHMDB
Nicotinate D-ribonucleosideHMDB
Nicotinate D-ribonucleotideHMDB
Nicotinate nucleotideHMDB
Nicotinate ribonucleotideHMDB
Nicotinate-D-ribonucleotideHMDB
Nicotinate-delta-ribonucleotideHMDB
Nicotinic acid ribonucleotideHMDB
Nicotinic acid ribotideHMDB
Nicotinic mononucleotideHMDB
Chemical FormulaC11H16NO9P
Average Molecular Weight337.2198
Monoisotopic Molecular Weight337.056267627
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 Name3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium
CAS Registry Number321-02-8
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)([O-])=O)[N+]1=CC=CC(C1)C(O)=O
InChI Identifier
InChI=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
InChI KeyOGCWVIVNTBZPBW-BHRXDNSCSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9722000000-018e28ddf721d5b8f3e5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000b-9321450000-a1a581b1c0db3e8a82f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1109000000-853a042b1707a4c36557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-7539000000-e8df8c1fb65e397a534dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002e-8910000000-7666464d7f3cabd48973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1109000000-924b50297114d22949c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-9101000000-5bedd125bd4b3f9df5aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0032-9000000000-78cf9bb7de438a8e5979View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001132
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022444
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01185
BioCyc IDNot Available
BiGG ID37018
Wikipedia LinkNot Available
METLIN ID6026
PubChem Compound53477721
PDB IDNot Available
ChEBI ID15763
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate with the same efficiency. Can use triazofurin monophosphate (TrMP) as substrate. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity, prefers NAD(+) and NaAD as substrates and degrades NADH, nicotinic acid adenine dinucleotide phosphate (NHD) and nicotinamide guanine dinucleotide (NGD) less effectively. Involved in the synthesis of ATP in the nucleus, together with PARP1, PARG and NUDT5. Nuclear ATP generation is required for extensive chromatin remodeling events that are energy-consuming. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NaADP(+) (By similarity). Protects against axonal degeneration following mechanical or toxic insults (By similarity).
Gene Name:
NMNAT1
Uniprot ID:
Q0VD50
Molecular weight:
32200.0
General function:
Coenzyme transport and metabolism
Specific function:
Nicotinamide/nicotinate-nucleotide adenylyltransferase that acts as an axon maintenance factor (By similarity). Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate but with a lower efficiency. Cannot use triazofurin monophosphate (TrMP) as substrate. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity prefers NAD(+), NADH and NaAD as substrates and degrades nicotinic acid adenine dinucleotide phosphate (NHD) less effectively. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NaADP(+) (By similarity). Axon survival factor required for the maintenance of healthy axons: acts by delaying Wallerian axon degeneration, an evolutionarily conserved process that drives the loss of damaged axons (By similarity).
Gene Name:
NMNAT2
Uniprot ID:
Q0VC59
Molecular weight:
34468.0
Reactions
Nicotinic acid mononucleotide + Adenosine triphosphate → Nicotinic acid adenine dinucleotide + Pyrophosphatedetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
O46411
Molecular weight:
64841.0
Reactions
Nicotinic acid mononucleotide + Water → Nicotinate D-ribonucleoside + Hydrogen phosphatedetails
General function:
Replication, recombination and repair
Specific function:
Hydrolyzes NAD(P)H to NMNH and AMP (2',5'-ADP), and diadenosine diphosphate to AMP. Has also activity towards NAD(P)(+), ADP-ribose and diadenosine triphosphate. May act to regulate the concentration of peroxisomal nicotinamide nucleotide cofactors required for oxidative metabolism in this organelle.
Gene Name:
NUDT12
Uniprot ID:
Q29RH3
Molecular weight:
50119.0
Reactions
Nicotinic acid adenine dinucleotide + Water → Nicotinic acid mononucleotide + Adenosine monophosphatedetails
Nicotinic acid adenine dinucleotide + Water →2 Nicotinic acid mononucleotidedetails
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the first step in the biosynthesis of NAD from nicotinic acid, the ATP-dependent synthesis of beta-nicotinate D-ribonucleotide from nicotinate and 5-phospho-D-ribose 1-phosphate. Helps prevent cellular oxidative stress via its role in NAD biosynthesis.
Gene Name:
NAPRT
Uniprot ID:
A5PK51
Molecular weight:
57871.0
General function:
Coenzyme transport and metabolism
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q3T063
Molecular weight:
31151.0
Reactions
Nicotinic acid mononucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
NMRK1
Uniprot ID:
F1N5H1
Molecular weight:
22612.0
Reactions
Nicotinate D-ribonucleoside + Adenosine triphosphate → Nicotinic acid mononucleotide + ADPdetails