Nicotinamide ribotide (CHEM021707)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:30 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021707
Identification
Common NameNicotinamide ribotide
ClassSmall Molecule
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 Nicotinamide ribotide by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme Nicotinamide ribotide adenylyltransferase (NMNAT, EC 2.7.7.1), a member of the nucleotidyltransferase alpha/beta-phosphodiesterase superfamily, catalyzes the reaction Nicotinamide ribotide + 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 Nicotinamide ribotide is an important metabolite for the maintenance of normal NAD biosynthesis, and circulating Nicotinamide ribotide levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171, 17983582)
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass334.219 g/mol
Monoisotopic Mass334.057 g/mol
CAS Registry Number1094-61-7
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
SMILESNC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-8902000000-75d46c23151f03298e05Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4920300000-f0eec1327b9e3e217fddSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1931000000-5aa0e5ba467b6bdbb57fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dj-6920000000-4720b1b8ab108dc1b499Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00mk-8903000000-042bd96d57e63adafe44Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-3900000000-013c2f02e48342e61b5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-3900000000-013c2f02e48342e61b5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1109000000-7e48df4297f6933ffc64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-7419000000-c70e04daa2249a30318cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9600000000-ec07884c9a438ebdba5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1009000000-623a45d318f08c622565Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9002000000-a9b586e58b5858c6d213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0032-9000000000-3fde5442f77c9f4b54b3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000229
FooDB IDFDB021912
Phenol Explorer IDNot Available
KNApSAcK IDC00019694
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID16171
PubChem Compound ID14180
Kegg Compound IDC00455
YMDB IDYMDB00138
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available