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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:13:47 UTC
HMDB IDHMDB0000229
Secondary Accession Numbers
  • HMDB00229
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
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
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
Mononucleotide, nicotinamideMeSH
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]-1λ⁵-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
DescriptionThis compound belongs to the class of chemical entities known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyridine nucleotides
Direct ParentNicotinamide nucleotides
Alternative Parents
Substituents
  • Nicotinamide-nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Nicotinamide
  • Pyridine carboxylic acid or derivatives
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyridine
  • Pyridinium
  • Alkyl phosphate
  • Vinylogous amide
  • Oxolane
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxamide group
  • 1,2-diol
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility4.16 mg/mLALOGPS
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
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified66.67 - 133.33 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)FemaleEpithelial ovarian cancer details
    UrineDetected and Quantified133.33 - 600 umol/mmol creatinineAdult (>18 years old)Both
    Sodium nitrate consumption
    details
    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 LinkHMDB0000229
    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