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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-01 16:24:03 UTC
HMDB IDHMDB0001132
Secondary Accession Numbers
  • HMDB0059646
  • HMDB01132
  • HMDB59646
Metabolite Identification
Common NameNicotinic acid mononucleotide
DescriptionNicotinic acid mononucleotide, also known as nicotinate ribonucleotide, 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. Nicotinic acid mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinic acid mononucleotide an intermediate in the cofactor biosynthesis and the nicotinate and nicotinamide metabolism pathways. It is a substrate for nicotinamide riboside kinase, ectonucleotide pyrophosphatase/phosphodiesterase, nicotinamide mononucleotide adenylyltransferase, 5'-nucleotidase, nicotinate-nucleotide pyrophosphorylase, and 5'(3')-deoxyribonucleotidase.
Structure
Data?1588350243
Synonyms
ValueSource
beta-Nicotinate D-ribonucleotideChEBI
Nicotinate ribonucleotideChEBI
Nicotinic acid ribonucleotideChEBI
b-Nicotinate D-ribonucleotideGenerator
b-Nicotinic acid D-ribonucleotideGenerator
beta-Nicotinic acid D-ribonucleotideGenerator
β-Nicotinate D-ribonucleotideGenerator
β-Nicotinic acid D-ribonucleotideGenerator
Nicotinic acid D-ribonucleotideGenerator
Nicotinate D-ribonucleotideChEBI
Nicotinate b-D-ribonucleotideGenerator
Nicotinate β-D-ribonucleotideGenerator
Nicotinic acid b-D-ribonucleotideGenerator
Nicotinic acid beta-D-ribonucleotideGenerator
Nicotinic acid β-D-ribonucleotideGenerator
Nicotinate mononucleotideMeSH
Nicotinic acid mononucleotideMeSH
Deamido nicotinamide ribonucleotideHMDB
Deamido-NMNHMDB
Nicotinic acid ribotideHMDB
Nicotinic mononucleotideHMDB
beta-Nicotinic acid mononucleotideHMDB
β-Nicotinic acid mononucleotideHMDB
Chemical FormulaC11H15NO9P
Average Molecular Weight336.2119
Monoisotopic Molecular Weight336.048442595
IUPAC Name3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional Name3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-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/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
InChI KeyJOUIQRNQJGXQDC-ZYUZMQFOSA-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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-9704000000-b4f3d91df4a5fb88cc5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000b-9221310000-f2425a1cc55147b91d2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1009000000-227e6a4729b96a705fa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-5239000000-223d08e3fd97af58d374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9500000000-db23a80f58b7ac9781fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1009000000-f16974a59d3ff46358d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9001000000-ca67d776dd7d3f5d4650Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5808f9bb378f2d60cd9bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02382
Phenol Explorer Compound IDNot Available
FooDB IDFDB022444
KNApSAcK IDC00007447
Chemspider ID108822
KEGG Compound IDC01185
BioCyc IDNICOTINATE_NUCLEOTIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound121992
PDB IDNot Available
ChEBI ID15763
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Only showing the first 10 proteins. There are 17 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
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
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
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
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
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
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
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
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
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
Reactions
Nicotinic acid adenine dinucleotide + Water → Adenosine monophosphate + Nicotinic acid mononucleotidedetails
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
Reactions
Nicotinic acid adenine dinucleotide + Water → Adenosine monophosphate + Nicotinic acid mononucleotidedetails
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
Reactions
Adenosine triphosphate + Nicotinic acid mononucleotide → Pyrophosphate + Nicotinic acid adenine dinucleotidedetails
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
Reactions
Adenosine triphosphate + Nicotinic acid mononucleotide → Pyrophosphate + Nicotinic acid adenine dinucleotidedetails
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
Reactions
Nicotinic acid mononucleotide + Pyrophosphate + CO(2) → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
Nicotinic acid mononucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails

Only showing the first 10 proteins. There are 17 proteins in total.