Nicotinamide ribotide
Nicotinamide 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 moleclie that plays a fundamental role as a cofactor in cellliar redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis. Circliating NMN levels may play an important role in regliating cell function in physiological and pathophysiological conditions. (PMID: 15078171 , 17983582 ).
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00229 (Nicotinamide ribotide)
C11H15N2O8P
334.2192
334.056601978
3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1λ⁵-pyridin-1-ylium
nmn zwitterion
1094-61-7
NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O
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
DAYLJWODMCOQEW-TURQNECASA-N
This 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.
Chemical entities
Organic compounds
Nucleosides, nucleotides, and analogues
Pyridine nucleotides
Nicotinamide nucleotides
Aromatic heteromonocyclic compounds
Detected and Quantified
Not Available
Solid
Predicted GC-MS Spectrum – GC-MSNot Available
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1931000000-5aa0e5ba467b6bdbb57fView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-00dj-6920000000-4720b1b8ab108dc1b499View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-00mk-8903000000-042bd96d57e63adafe44View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-3900000000-013c2f02e48342e61b5eView in MoNA
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
1H NMR SpectrumNot Available
1H NMR SpectrumNot Available
13C NMR SpectrumNot Available
[1H,1H] 2D NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Normal
Sodium nitrate consumption
- Jansen EH, van den Berg RH, Boink AB, Hegger C, Melienbelt J: A new physiological biomarker for nitrate exposure in humans. Toxicol Lett. 1995 May;77(1-3):265-9. [PubMed:7618150 ]
None
Not Available
Not Available
Not Available
Not Available
FDB021912
Not Available
13553
C00455
NICOTINAMIDE_NUCLEOTIDE
35022
Not Available
HMDB00229
HMDB00229
5238
14180
Not Available
16171
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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