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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 20:20:49 UTC
HMDB IDHMDB0001132
Secondary Accession Numbers
  • HMDB01132
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 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
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
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
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
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022444
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01185
BioCyc IDNICOTINATE_NUCLEOTIDE
BiGG ID37018
Wikipedia LinkNot Available
METLIN ID6026
PubChem Compound53477721
PDB ID1L4F
ChEBI ID15763
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Only showing the first 10 proteins. There are 15 proteins in total.

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

Only showing the first 10 proteins. There are 15 proteins in total.