Record Information
Version1.0
Creation Date2016-09-30 22:27:05 UTC
Update Date2020-05-21 16:28:55 UTC
BMDB IDBMDB0000229
Secondary Accession Numbers
  • BMDB00229
Metabolite Identification
Common NameNicotinamide ribotide
DescriptionNicotinamide ribotide, also known as NMN or beta-NMN, belongs to the class of organic compounds known as nicotinamide ribotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof. Nicotinamide ribotide is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide ribotide exists in all eukaryotes, ranging from yeast to humans. Nicotinamide ribotide participates in a number of enzymatic reactions, within cattle. In particular, Nicotinamide ribotide can be biosynthesized from nicotinamide riboside through the action of the enzyme cytosolic purine 5'-nucleotidase. In addition, Nicotinamide ribotide can be biosynthesized from niacinamide and phosphoribosyl pyrophosphate; which is mediated by the enzyme nicotinamide phosphoribosyltransferase. In cattle, nicotinamide ribotide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
3-(Aminocarbonyl)-1-(5-O-phosphonato-beta-D-ribofuranosyl)pyridiniumChEBI
3-(Aminocarbonyl)-1-(5-O-phosphono-beta-D-ribofuranosyl)pyridinium, inner saltChEBI
beta-Nicotinamide D-ribonucleotideChEBI
beta-Nicotinamide mononucleotideChEBI
beta-Nicotinamide ribonucleotideChEBI
Nicotinamide D-ribonucleotideChEBI
Nicotinamide mononucleotideChEBI
Nicotinamide nucleotideChEBI
Nicotinamide ribonucleotideChEBI
NMNChEBI
3-(Aminocarbonyl)-1-(5-O-phosphonato-b-D-ribofuranosyl)pyridiniumGenerator
3-(Aminocarbonyl)-1-(5-O-phosphonato-β-D-ribofuranosyl)pyridiniumGenerator
3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)pyridinium, inner saltGenerator
3-(Aminocarbonyl)-1-(5-O-phosphono-β-D-ribofuranosyl)pyridinium, inner saltGenerator
b-Nicotinamide D-ribonucleotideGenerator
Β-nicotinamide D-ribonucleotideGenerator
b-Nicotinamide mononucleotideGenerator
Β-nicotinamide mononucleotideGenerator
b-Nicotinamide ribonucleotideGenerator
Β-nicotinamide ribonucleotideGenerator
Mononucleotide, nicotinamideMeSH
3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-pyridinium hydroxide inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-pyridinium inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-pyridinium hydroxide inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-pyridinium inner saltHMDB
3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner saltHMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner saltHMDB
b-D-NMNHMDB
b-NMNHMDB
beta-delta-NMNHMDB
beta-NMNHMDB
Nicotinamide ribonucleoside 5'-phosphateHMDB
BibenzoylHMDB
DiphenylethanedioneHMDB
DiphenylglyoxalHMDB
1,2-Diphenylethane-1,2-dioneHMDB
Diphenylethane-1,2-dioneHMDB
Diphenyl-alpha-beta-ketoneHMDB
Phosphatidylinositol 4,5-bisphosphoric acidHMDB
Diadenosine triphosphoric acidHMDB
Adenosine (5')triphospho(5')adenosineHMDB
Adenosine 5'-triphosphate 5'-adenosineHMDB
Adenosine(3)triphosphate adenosineHMDB
Adenosine(5')triphospho(5')adenosineHMDB
Bis(adenosine)-5'-triphosphateHMDB
p(1),p(3)-Bis(5'-adenosyl) trihydrogen triphosphateHMDB
p(1),p(3)-Bis(5'-adenosyl) triphosphateHMDB
p(1)-p(3)-Bis(5'-adenosyl) triphosphateHMDB
P1,P3-Bis(5'-adenosyl) triphosphateHMDB
Ap3aHMDB
5'Ap3aHMDB
p(1),(P3)-Bis(5'-adenosyl)triphosphateHMDB
ApppAHMDB
TetrahydrofolateHMDB
(6S)-TetrahydrofolateHMDB
(6S)-Tetrahydrofolic acidHMDB
5,6,7,8-TetrahydrofolateHMDB
5,6,7,8-Tetrahydrofolic acidHMDB
Tetra-H-folateHMDB
TetrahydrafolateHMDB
Tetrahydropteroyl mono-L-glutamateHMDB
TetrahydropteroylglutamateHMDB
1,4-ButanediamineHMDB
1,4-ButylenediamineHMDB
1,4-DIAMINOBUTANEHMDB
1,4-TetramethylenediamineHMDB
Butane-1,4-diamineHMDB
ButylenediamineHMDB
H2N(CH2)4nh2HMDB
PutrescinHMDB
PutrescinaHMDB
PutreszinHMDB
TetramethylendiaminHMDB
TetramethylenediamineHMDB
1,4-ButanediammoniumHMDB
TetramethyldiamineHMDB
1,4 DiaminobutaneHMDB
1,4 ButanediamineHMDB
Chemical FormulaC11H15N2O8P
Average Molecular Weight334.2192
Monoisotopic Molecular Weight334.056601978
IUPAC Name3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional Name3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium
CAS Registry Number1094-61-7
SMILES
NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1
InChI KeyDAYLJWODMCOQEW-TURQNECASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyridine nucleotides
Sub ClassNicotinamide nucleotides
Direct ParentNicotinamide nucleotides
Alternative Parents
Substituents
  • Nicotinamide-nucleotide
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Nicotinamide
  • Pyridine carboxylic acid or derivatives
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyridinium
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • 1,2-diol
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
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-1.5ALOGPS
logP-6.2ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area166.25 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.59 m³·mol⁻¹ChemAxon
Polarizability28.77 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-006t-8902000000-75d46c23151f03298e05View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4920300000-f0eec1327b9e3e217fddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1931000000-5aa0e5ba467b6bdbb57fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dj-6920000000-4720b1b8ab108dc1b499View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00mk-8903000000-042bd96d57e63adafe44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-3900000000-013c2f02e48342e61b5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-3900000000-013c2f02e48342e61b5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1109000000-7e48df4297f6933ffc64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-7419000000-c70e04daa2249a30318cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9600000000-ec07884c9a438ebdba5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1009000000-623a45d318f08c622565View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9002000000-a9b586e58b5858c6d213View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0032-9000000000-3fde5442f77c9f4b54b3View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000229
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021912
KNApSAcK IDC00019694
Chemspider IDNot Available
KEGG Compound IDC00455
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14180
PDB IDNot Available
ChEBI ID16171
References
Synthesis ReferenceLiu, Rihe; Visscher, Johannes. A novel preparation of nicotinamide mononucleotide. Nucleosides & Nucleotides (1994), 13(5), 1215-16.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Coenzyme transport and metabolism
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. Involved in the synthesis of ATP in the nucleus, together with PARP1, PARG and NUDT5. Nuclear ATP generation is required for extensive chromatin remodeling events that are energy-consuming. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NaADP(+) (By similarity). Protects against axonal degeneration following mechanical or toxic insults (By similarity).
Gene Name:
NMNAT1
Uniprot ID:
Q0VD50
Molecular weight:
32200.0
General function:
Coenzyme transport and metabolism
Specific function:
Nicotinamide/nicotinate-nucleotide adenylyltransferase that acts as an axon maintenance factor (By similarity). 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(+) (By similarity). Axon survival factor required for the maintenance of healthy axons: acts by delaying Wallerian axon degeneration, an evolutionarily conserved process that drives the loss of damaged axons (By similarity).
Gene Name:
NMNAT2
Uniprot ID:
Q0VC59
Molecular weight:
34468.0
Reactions
NAD + Pyrophosphate → Nicotinamide ribotide + Adenosine triphosphatedetails
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
General function:
Replication, recombination and repair
Specific function:
Hydrolyzes NAD(P)H to NMNH and AMP (2',5'-ADP), and diadenosine diphosphate to AMP. Has also activity towards NAD(P)(+), ADP-ribose and diadenosine triphosphate. May act to regulate the concentration of peroxisomal nicotinamide nucleotide cofactors required for oxidative metabolism in this organelle.
Gene Name:
NUDT12
Uniprot ID:
Q29RH3
Molecular weight:
50119.0
Reactions
NAD + Water → Nicotinamide ribotide + Adenosine monophosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
NAMPT
Uniprot ID:
F1MJ80
Molecular weight:
53675.0
Reactions
Niacinamide + Phosphoribosyl pyrophosphate → Nicotinamide ribotide + Pyrophosphatedetails