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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2008-08-12 13:40:35 UTC
Update Date2020-07-17 20:20:58 UTC
HMDB IDHMDB0006809
Secondary Accession Numbers
  • HMDB06809
Metabolite Identification
Common NameNicotinic acid ribonucleoside
DescriptionNicotinate D-ribonucleoside, also known as nicotinic acid riboside or beta-D-ribosylnicotinate, belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Nicotinate D-ribonucleoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinate D-ribonucleoside exists in all living species, ranging from bacteria to humans. Within humans, nicotinate D-ribonucleoside participates in a number of enzymatic reactions. In particular, nicotinate D-ribonucleoside can be converted into nicotinic acid mononucleotide; which is catalyzed by the enzyme nicotinamide riboside kinase 1. In addition, nicotinate D-ribonucleoside can be biosynthesized from nicotinic acid mononucleotide; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. A pyridine nucleoside consisting of nicotinic acid with a beta-D-ribofuranosyl moiety at the 1-position. In humans, nicotinate D-ribonucleoside is involved in nicotinate and nicotinamide metabolism.
Structure
Data?1595017258
Synonyms
ValueSource
Nicotinic acid ribosideChEBI
beta-D-RibosylnicotinateKegg
Nicotinate ribosideGenerator
b-D-RibosylnicotinateGenerator
b-D-Ribosylnicotinic acidGenerator
beta-D-Ribosylnicotinic acidGenerator
Β-D-ribosylnicotinateGenerator
Β-D-ribosylnicotinic acidGenerator
Nicotinic acid D-ribonucleosideGenerator
D-RibosylnicotinateHMDB
Nicotinic acid riboseHMDB
RibosylnicotinateHMDB
Nicotinate ribonucleosideHMDB
Nicotinate riboseHMDB
Nicotinic acid ribonucleosideHMDB
3-Carboxy-1-beta-D-ribofuranosylpyridiniumHMDB
3-Carboxy-1-β-D-ribofuranosylpyridiniumHMDB
Nicotinic ribosideHMDB
Chemical FormulaC11H14NO6
Average Molecular Weight256.232
Monoisotopic Molecular Weight256.082112185
IUPAC Name3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional Name3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
CAS Registry Number4013-06-3
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)[N+]1=CC=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/p+1/t7-,8-,9-,10-/m1/s1
InChI KeyPUEDDPCUCPRQNY-ZYUZMQFOSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pentose monosaccharide
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Monosaccharide
  • Pyridine
  • Pyridinium
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

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 Solubility5.34 g/LALOGPS
logP-1.9ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area111.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.01 m³·mol⁻¹ChemAxon
Polarizability24.21 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, Positivesplash10-009f-9640000000-9ecd90015c00728b3b07Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fa9-9442740000-0573803f81575b22f5c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-384ec325284b36db888bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2190000000-5ab972cf9d81893b8388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9510000000-8e2f234fa7933273a714Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-c2d0a64c0eb3d4ae2bfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0490000000-bb44dd196c6e9a647df7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgu-9600000000-d17b549da8f5e8b2dd2bSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024094
KNApSAcK IDNot Available
Chemspider ID141636
KEGG Compound IDC05841
BioCyc IDCPD-8259
BiGG ID46613
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161234
PDB IDNot Available
ChEBI ID27748
Food Biomarker OntologyNot Available
VMH IDNICRNS
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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 magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
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:
P49902
Molecular weight:
64969.2
Reactions
Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphatedetails
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
Reactions
Nicotinic acid ribonucleoside + Phosphate → Nicotinic acid + Ribose 1-phosphate + Hydrogen Iondetails
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
Reactions
Adenosine triphosphate + Nicotinic acid ribonucleoside → ADP + nicotinate beta-D-ribonucleotidedetails
Nicotinic acid mononucleotide + ADP → Nicotinic acid ribonucleoside + Adenosine triphosphatedetails
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
Reactions
Adenosine triphosphate + Nicotinic acid ribonucleoside → ADP + nicotinate beta-D-ribonucleotidedetails
Nicotinic acid mononucleotide + ADP → Nicotinic acid ribonucleoside + Adenosine triphosphatedetails