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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:53 UTC
HMDB IDHMDB01132
Secondary Accession NumbersNone
Metabolite Identification
Common NameNicotinic acid mononucleotide
DescriptionNicotinic acid mononucleotide is an intermediate in the metabolism of Nicotinate and nicotinamide. It is a substrate for Ectonucleotide pyrophosphatase/phosphodiesterase 2, Ectonucleotide pyrophosphatase/phosphodiesterase 1, Nicotinamide mononucleotide adenylyltransferase 3, Cytosolic 5'-nucleotidase IA, Cytosolic 5'-nucleotidase IB, Nicotinate-nucleotide pyrophosphorylase, 5'(3')-deoxyribonucleotidase (cytosolic type), Cytosolic purine 5'-nucleotidase, Nicotinamide mononucleotide adenylyltransferase 2, Ectonucleotide pyrophosphatase/phosphodiesterase 3, 5'-nucleotidase, 5'(3')-deoxyribonucleotidase (mitochondrial) and Nicotinamide mononucleotide adenylyltransferase 1.
Structure
Thumb
Synonyms
ValueSource
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 mononucleotideHMDB
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 KeyInChIKey=OGCWVIVNTBZPBW-BHRXDNSCSA-N
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
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic zwitterion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
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
Water Solubility9.83 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.91 m3·mol-1ChemAxon
Polarizability28.69 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048map00760
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022444
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01185
BioCyc IDNICOTINATE_NUCLEOTIDE
BiGG ID37018
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01132
Metagene LinkHMDB01132
METLIN ID6026
PubChem Compound53477721
PDB ID1L4F
ChEBI ID15763
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
General function:
Involved in nucleotidyltransferase activity
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. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following mechanical or toxic insults.
Gene Name:
NMNAT1
Uniprot ID:
Q9HAN9
Molecular weight:
31932.22
General function:
Involved in nucleotidyltransferase activity
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. Can also use GTP and ITP as nucleotide donors. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity, can use NAD (+), NADH, NAAD, nicotinic acid adenine dinucleotide phosphate (NHD), nicotinamide guanine dinucleotide (NGD) as substrates. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following injury.
Gene Name:
NMNAT3
Uniprot ID:
Q96T66
Molecular weight:
18255.08
General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q15274
Molecular weight:
30815.28
General function:
Involved in nucleotidyltransferase activity
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 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(+).
Gene Name:
NMNAT2
Uniprot ID:
Q9BZQ4
Molecular weight:
34438.38
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
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). The enzyme also phosphorylates the antitumor drugs tiazofurin and 3-deazaguanosine.
Gene Name:
NMRK1
Uniprot ID:
Q9NWW6
Molecular weight:
20152.76
General function:
Involved in hydrolase activity
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:
Q9BQG2
Molecular weight:
52075.475
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN). Reduces laminin matrix deposition and cell adhesion to laminin, but not to fibronectin. Involved in the regulation of PXN at the protein level and of PXN tyrosine phosphorylation. May play a role in the regulation of terminal myogenesis.
Gene Name:
NMRK2
Uniprot ID:
Q9NPI5
Molecular weight:
26045.335
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the conversion of nicotinic acid (NA) to NA mononucleotide (NaMN). Essential for NA to increase cellular NAD levels and prevent oxidative stress of the cells.
Gene Name:
NAPRT1
Uniprot ID:
Q6XQN6
Molecular weight:
57577.575