Showing metabocard for Nicotinamide riboside (BMDB0000855)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:34 UTC
Update Date2020-05-21 16:28:55 UTC
BMDB IDBMDB0000855
Secondary Accession Numbers
  • BMDB00855
Metabolite Identification
Common NameNicotinamide riboside
DescriptionNicotinamide riboside, also known as N-ribosylnicotinamide or SRT-647, 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). Nicotinamide riboside is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Nicotinamide riboside participates in a number of enzymatic reactions, within cattle. In particular, Nicotinamide riboside and phosphoric acid can be biosynthesized from niacinamide and ribose-1-arsenate; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, Nicotinamide riboside can be converted into nicotinamide ribotide; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In cattle, nicotinamide riboside is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(beta-D-Ribofuranosyl)nicotinamideChEBI
beta-Nicotinamide D-ribosideChEBI
Nicotinamide ribonucleosideChEBI
Nicotinamide riboseChEBI
Nicotinamide-beta-ribosideChEBI
N-RibosylnicotinamideKegg
1-(b-D-Ribofuranosyl)nicotinamideGenerator
1-(Β-D-ribofuranosyl)nicotinamideGenerator
b-Nicotinamide D-ribosideGenerator
Β-nicotinamide D-ribosideGenerator
Nicotinamide-b-ribosideGenerator
Nicotinamide-β-ribosideGenerator
1-b-D-Ribosyl-3-pyridinecarboxamideHMDB
1-beta-D-Ribosyl-3-pyridinecarboxamideHMDB
1-beta-delta-Ribosyl-3-pyridinecarboxamideHMDB
3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-pyridiniumHMDB
3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-pyridiniumHMDB
RibosylnicotinamideHMDB
SRT-647HMDB
SRT 647HMDB
Chemical FormulaC11H15N2O5
Average Molecular Weight255.2472
Monoisotopic Molecular Weight255.0980966
IUPAC Name3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional Name3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
CAS Registry Number1341-23-7
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1
InChI KeyJLEBZPBDRKPWTD-TURQNECASA-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
  • Nicotinamide
  • Pyridine carboxylic acid or derivatives
  • Monosaccharide
  • Pyridine
  • Pyridinium
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxamide group
  • Primary carboxylic acid amide
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-6.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.39ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.83 m³·mol⁻¹ChemAxon
Polarizability24.83 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Kurt J. Boudonck,...
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000855
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022281
KNApSAcK IDNot Available
Chemspider ID388956
KEGG Compound IDC03150
BioCyc IDNICOTINAMIDE_RIBOSE
BiGG ID41300
Wikipedia LinkNicotinamide riboside
METLIN ID5818
PubChem Compound439924
PDB IDNot Available
ChEBI ID15927
References
Synthesis ReferenceFranchetti, Palmarisa; Pasqualini, Michela; Petrelli, Riccardo; Ricciutelli, Massimo; Vita, Patrizia; Cappellacci, Loredana. Stereoselective synthesis of nicotinamide b-riboside and nucleoside analogs. Bioorganic & Medicinal Chemistry Letters (2004), 14(18), 4655-4658 Yang, T, Chan NY, Sauve AA. Syntheses of nicotinamide riboside and deriviatives.. J. Med Chem. 50:6458-61 (2007)..
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

Enzymes

Enzyme Details
1. Cytosolic purine 5'-nucleotidase
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
Nicotinamide riboside + Hydrogen phosphate → Nicotinamide ribotide + Waterdetails
Enzyme Details
2. Purine nucleoside phosphorylase
General function:
Nucleotide transport and metabolism
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:
P55859
Molecular weight:
32037.0
Reactions
Niacinamide + Ribose-1-arsenate → Nicotinamide riboside + Hydrogen phosphatedetails