Record Information
Version1.0
Created at2020-04-17 18:44:58 UTC
Updated at2020-11-18 16:38:53 UTC
CannabisDB IDCDB004867
Secondary Accession NumbersNot Available
Cannabis Compound 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). A pyridine nucleoside consisting of nicotinamide with a beta-D-ribofuranosyl moiety at the 1-position. Nicotinamide riboside is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Within humans, nicotinamide riboside participates in a number of enzymatic reactions. In particular, nicotinamide riboside and phosphoric acid can be biosynthesized from niacinamide and ribose-1-arsenate through its interaction with the enzyme purine nucleoside phosphorylase. In addition, nicotinamide riboside can be converted into nicotinamide ribotide through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In humans, nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Outside of the human body, Nicotinamide riboside has been detected, but not quantified in, milk (cow). This could make nicotinamide riboside a potential biomarker for the consumption of these foods. Nicotinamide riboside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight255.25
Monoisotopic Molecular Weight255.0981
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
Disposition

Source:

Biological location:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNicotinamide riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-070f-9530000000-71d9e02ee640bb800185Spectrum
Predicted GC-MSNicotinamide riboside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6r-9825400000-99de0fc632f408e32a12Spectrum
Predicted GC-MSNicotinamide riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide riboside, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0190000000-51bf764225f08b566d36Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0290000000-ffbe280293f874204044Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-05fr-0970000000-1714e669425e34d3754aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0920000000-77ef12950b3152d752c8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-b14d15851532222ba74aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-0900000000-277d95be8f0485eb3ce5Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-0900000000-354c1f3978635e5109bbSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-0900000000-ea5e376f71c6414964bcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00di-0900000000-6b289ae1c5f53e92f774Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-00di-1900000000-6ad92fa16e2cca17f959Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00di-1900000000-cee8757ed6b406ccf044Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-00di-2900000000-78f21d967892a0d9ab85Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-00di-3900000000-cd1f66bfc8ded7bd098eSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-00e9-8900000000-5a6bc8100043575c6a58Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-00ai-9200000000-aedd3c5bf179b666a6aeSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-003r-9000000000-22053c801abdfaf5f562Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0fai-9000000000-b6b4b7e819e08c863a9aSpectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-00di-0900000000-3364e345334aa7f5a742Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-004i-9000000000-3bf262f96423e85a1756Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-e25d1beb47cb1fe9e4cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-3090000000-03687e9ef697eda1d6c8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9300000000-2755bde4df843d2227f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-809be1146b2a2c8d96a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1390000000-2fc72cf0619f182e044fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k96-9300000000-4d5b96b192f3484b1b8aSpectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Ribosyldihydronicotinamide dehydrogenase [quinone]NQO26p25.2P16083 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Purine nucleoside phosphorylasePNP14q13.1P00491 details
Nicotinamide riboside kinase 1NMRK19q21.13Q9NWW6 details
Nicotinamide riboside kinase 2NMRK219p13.3Q9NPI5 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Ribosyldihydronicotinamide dehydrogenase [quinone]NQO26p25.2P16083 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Nicotinamide riboside kinase 1NMRK19q21.13Q9NWW6 details
Nicotinamide riboside kinase 2NMRK219p13.3Q9NPI5 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000855
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Only showing the first 10 proteins. There are 21 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
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 electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular weight:
25918.4
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 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
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
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

Only showing the first 10 proteins. There are 21 proteins in total.