Record Information
Version1.0
Creation date2011-09-21 00:05:02 UTC
Update date2015-10-09 22:30:48 UTC
Primary IDFDB021912
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNicotinamide ribotide
DescriptionNicotinamide ribotide (NMN) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. Mammals predominantly use nicotinamide rather than nicotinic acid as a precursor for NAD biosynthesis. Instead of the deamidation to nicotinic acid, nicotinamide is directly converted to NMN by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme nicotinamide mononucleotide adenylyltransferase (NMNAT, EC 2.7.7.1), a member of the nucleotidyltransferase alpha/beta-phosphodiesterase superfamily, catalyzes the reaction NMN + ATP = Nicotinamide adenine dinucleotide (NAD) + PPi, representing the final step in the biosynthesis of NAD, a molecule playing a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis, and circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171, 17983582) [HMDB]
CAS Number1094-61-7
Structure
Thumb
Synonyms
SynonymSource
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
3-(Aminocarbonyl)-1-(5-O-onato-b-D-ribofuranosyl)pyridiniumGenerator
3-(Aminocarbonyl)-1-(5-O-onato-beta-D-ribofuranosyl)pyridiniumChEBI
3-(Aminocarbonyl)-1-(5-O-onato-β-D-ribofuranosyl)pyridiniumGenerator
3-(Aminocarbonyl)-1-(5-O-ONO-b-D-ribofuranosyl)-pyridinium hydroxide inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-ONO-b-D-ribofuranosyl)-pyridinium inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-ONO-b-D-ribofuranosyl)pyridinium, inner saltGenerator
3-(Aminocarbonyl)-1-(5-O-ONO-beta-D-ribofuranosyl)pyridinium, inner saltChEBI
3-(Aminocarbonyl)-1-(5-O-ONO-beta-delta-ribofuranosyl)-pyridinium hydroxide inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-ONO-beta-delta-ribofuranosyl)-pyridinium inner saltHMDB
3-(Aminocarbonyl)-1-(5-O-ONO-β-D-ribofuranosyl)pyridinium, inner saltGenerator
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'-ate inner saltHMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ate inner saltHMDB
Nicotinamide ribonucleoside 5'-ateHMDB
β-nicotinamide D-ribonucleotideGenerator
β-nicotinamide mononucleotideGenerator
β-nicotinamide ribonucleotideGenerator
Predicted Properties
PropertyValueSource
Water Solubility4.16 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H15N2O8P
IUPAC name3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium
InChI IdentifierInChI=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
Isomeric SMILESNC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O
Average Molecular Weight334.2192
Monoisotopic Molecular Weight334.056601978
Classification
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNicotinamide ribotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006t-8902000000-75d46c23151f03298e05Spectrum
Predicted GC-MSNicotinamide ribotide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-4920300000-f0eec1327b9e3e217fddSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1931000000-5aa0e5ba467b6bdbb57f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dj-6920000000-4720b1b8ab108dc1b4992012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00mk-8903000000-042bd96d57e63adafe442012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-3900000000-013c2f02e48342e61b5e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-3900000000-013c2f02e48342e61b5e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1109000000-7e48df4297f6933ffc642016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-7419000000-c70e04daa2249a30318c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9600000000-ec07884c9a438ebdba5a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1009000000-623a45d318f08c6225652016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9002000000-a9b586e58b5858c6d2132016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0032-9000000000-3fde5442f77c9f4b54b32016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID13553
ChEMBL IDCHEMBL610238
KEGG Compound IDC00455
Pubchem Compound ID14180
Pubchem Substance IDNot Available
ChEBI ID16171
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00229
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35022
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytosolic 5'-nucleotidase 3NT5C3Q9H0P0
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048 map00760
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference