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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-12 16:32:17 UTC
HMDB IDHMDB00229
Secondary Accession NumbersNone
Metabolite Identification
Common 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), which is 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. NAD is a molecule that plays a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis. Circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171 , 17983582 ).
Structure
Thumb
Synonyms
  1. 3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium hydroxide inner salt
  2. 3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt
  3. 3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium hydroxide inner salt
  4. 3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt
  5. 3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
  6. 3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
  7. b-D-NMN
  8. b-NMN
  9. beta-delta-NMN
  10. beta-NMN
  11. Nicotinamide D-ribonucleotide
  12. Nicotinamide mononucleotide
  13. Nicotinamide ribonucleoside 5'-phosphate
  14. Nicotinamide ribonucleotide
  15. NMN
Chemical FormulaC11H15N2O8P
Average Molecular Weight334.2192
Monoisotopic Molecular Weight334.056601978
IUPAC Name3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1$l^{5}-pyridin-1-ylium
Traditional Namenmn zwitterion
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
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyridine Nucleotides
Sub ClassNicotinamide Nucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Organic Compounds
  • nicotinamide mononucleotide(ChEBI)
Substituents
  • 1,2 Diol
  • Carboxamide Group
  • Glycosyl Compound
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Primary Carboxylic Acid Amide
  • Pyridine
  • Pyridinium
  • Saccharide
  • Secondary Alcohol
Direct ParentNicotinamide Nucleotides
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
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
Water Solubility4.16ALOGPS
logP-1.5ALOGPS
logP-6.2ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area166.25 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.59 m3·mol-1ChemAxon
Polarizability28.78 Å3ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Placenta
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048map00760
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified66.67 - 133.33 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified133.33 - 600 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References
Sodium nitrate consumption
  1. Jansen EH, van den Berg RH, Boink AB, Hegger C, Meulenbelt J: A new physiological biomarker for nitrate exposure in humans. Toxicol Lett. 1995 May;77(1-3):265-9. Pubmed: 7618150
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021912
KNApSAcK IDNot Available
Chemspider ID13553
KEGG Compound IDC00455
BioCyc IDNICOTINAMIDE_NUCLEOTIDE
BiGG ID35022
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00229
Metagene LinkHMDB00229
METLIN ID5238
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)Download (PDF)
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  2. Schuberth J: Volatile compounds detected in blood of drunk drivers by headspace/capillary gas chromatography/ion trap mass spectrometry. Biol Mass Spectrom. 1991 Nov;20(11):699-702. Pubmed: 1799580
  3. Emanuelli M, Raffaelli N, Amici A, Balducci E, Natalini P, Ruggieri S, Magni G: The antitumor drug, 1,3-bis(2-chloroethyl)-1-nitroso-urea, inactivates human nicotinamide mononucleotide adenylyltransferase. Biochem Pharmacol. 1995 Feb 14;49(4):575-9. Pubmed: 7872964
  4. Moriya F, Hashimoto Y: Postmortem production of ethanol and n-propanol in the brain of drowned persons. Am J Forensic Med Pathol. 2004 Jun;25(2):131-3. Pubmed: 15166764
  5. Magni G, Amici A, Emanuelli M, Orsomando G, Raffaelli N, Ruggieri S: Structure and function of nicotinamide mononucleotide adenylyltransferase. Curr Med Chem. 2004 Apr;11(7):873-85. Pubmed: 15078171
  6. Revollo JR, Korner A, Mills KF, Satoh A, Wang T, Garten A, Dasgupta B, Sasaki Y, Wolberger C, Townsend RR, Milbrandt J, Kiess W, Imai S: Nampt/PBEF/Visfatin regulates insulin secretion in beta cells as a systemic NAD biosynthetic enzyme. Cell Metab. 2007 Nov;6(5):363-75. Pubmed: 17983582

Enzymes

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 catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
General function:
Involved in nucleotidyltransferase activity
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. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following mechanical or toxic insults.
Gene Name:
NMNAT1
Uniprot ID:
Q9HAN9
Molecular weight:
31932.22
General function:
Involved in nucleotidyltransferase activity
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. Can also use GTP and ITP as nucleotide donors. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity, can use NAD (+), NADH, NAAD, nicotinic acid adenine dinucleotide phosphate (NHD), nicotinamide guanine dinucleotide (NGD) as substrates. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following injury.
Gene Name:
NMNAT3
Uniprot ID:
Q96T66
Molecular weight:
18255.08
General function:
Involved in nucleotidyltransferase activity
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 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(+).
Gene Name:
NMNAT2
Uniprot ID:
Q9BZQ4
Molecular weight:
34438.38
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 hydrolase activity
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:
Q9BQG2
Molecular weight:
52075.475
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to yield nicotinamide mononucleotide, an intermediate in the biosynthesis of NAD. It is the rate limiting component in the mammalian NAD biosynthesis pathway (By similarity).
Gene Name:
NAMPT
Uniprot ID:
P43490
Molecular weight:
55520.8