Nicotinamide ribotide (ECMDB00229) (M2MDB000095)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:24:17 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Nicotinamide ribotide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Nicotinamide ribotide (NMN) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. 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) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C11H15NO9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 336.2119 Monoisotopic: 336.048442595 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | JOUIQRNQJGXQDC-ZYUZMQFOSA-O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/p+1/t7-,8-,9-,10-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 1094-61-7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | 3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | 3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CC=CC(=C1)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | This compound belongs to the class of organic compounds known as nicotinic acid nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinic acid or a derivative thereof. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Pyridine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Nicotinic acid nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Nicotinic acid nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + Pyrophosphate 2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide <> Nicotinic acid adenine dinucleotide + Pyrophosphate Adenosine triphosphate + Water + Nicotinic acid + Phosphoribosyl pyrophosphate > ADP + Nicotinamide ribotide + Phosphate + Pyrophosphate Dimethylbenzimidazole + Nicotinamide ribotide <> N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Hydrogen ion + Nicotinic acid NAD + Water <> Adenosine monophosphate + Nicotinamide ribotide Adenosine triphosphate + Nicotinamide ribotide <> Pyrophosphate + NAD Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate Nicotinamide ribotide + Water <> Nicotinamide riboside + Phosphate Nicotinic acid adenine dinucleotide + Water <> Adenosine monophosphate + Nicotinamide ribotide Adenosine triphosphate + Nicotinamide ribotide <> Pyrophosphate + Nicotinic acid adenine dinucleotide Nicotinamide ribotide + Water <> Nicotinate D-ribonucleoside + Phosphate Nicotinamide ribotide + Pyrophosphate + Carbon dioxide <> Quinolinic acid + Phosphoribosyl pyrophosphate Hydrogen ion + Nicotinamide ribotide + Adenosine triphosphate <> NAD + Pyrophosphate Nicotinamide ribotide + Dimethylbenzimidazole > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole DNA<sub><i>n</i></sub> + (deoxynucleotides)<sub>(m)</sub> + NAD > (deoxynucleotides)<sub>(m)</sub> + Nicotinamide ribotide + Adenosine monophosphate Water + NAD > Hydrogen ion + Nicotinamide ribotide + Adenosine monophosphate Hydrogen ion + Adenosine triphosphate + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotide Nicotinamide ribotide + Pyrophosphate < Hydrogen ion + Nicotinic acid + Phosphoribosyl pyrophosphate Nicotinamide ribotide + Water > Hydrogen ion + Nicotinamide ribotide + Ammonia Nicotinamide ribotide + Water > Hydrogen ion + Nicotinamide ribotide + Ammonia Water + Nicotinamide ribotide <> Hydrogen ion + D-Ribose-5-phosphate + Niacinamide Nicotinamide ribotide + Pyrophosphate + Carbon dioxide < Phosphoribosyl pyrophosphate + Quinolinic acid + Hydrogen ion Nicotinamide riboside + Adenosine triphosphate > Hydrogen ion + Nicotinamide ribotide + ADP Nicotinamide ribotide + Dimethylbenzimidazole > Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole More...Nicotinamide ribotide + Pyrophosphate + Carbon dioxide > Quinolinic acid + Phosphoribosyl pyrophosphate Adenosine triphosphate + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotide Nicotinamide ribotide + Pyrophosphate > Nicotinic acid + Phosphoribosyl pyrophosphate NMN + Water <> Nicotinamide ribotide + Ammonia Quinolinic acid + Hydrogen ion + Phosphoribosyl pyrophosphate > Carbon dioxide + Pyrophosphate + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide nicotinate beta-D-ribonucleotide + Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotide Nicotinic acid + Water + Adenosine triphosphate + Phosphoribosyl pyrophosphate > Phosphate + Adenosine diphosphate + Pyrophosphate + nicotinate beta-D-ribonucleotide + ADP + Nicotinamide ribotide beta-nicotinamide D-ribonucleotide + Water + NMN > Ammonium + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide Dimethylbenzimidazole + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN NAD + Water <> Adenosine monophosphate + Nicotinamide ribotide NMN + Water <> Nicotinamide ribotide + Ammonia Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + Pyrophosphate 2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN 2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Liu, Rihe; Visscher, Johannes. A novel preparation of nicotinamide mononucleotide. Nucleosides & Nucleotides (1994), 13(5), 1215-16. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in hydrolase activity
- Specific function:
- Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
- Gene Name:
- ushA
- Uniprot ID:
- P07024
- Molecular weight:
- 60824
Reactions
| UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate. |
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the reversible adenylation of nicotinate mononucleotide (NaMN) to nicotinic acid adenine dinucleotide (NaAD)
- Gene Name:
- nadD
- Uniprot ID:
- P0A752
- Molecular weight:
- 24528
Reactions
| ATP + beta-nicotinate-D-ribonucleotide = diphosphate + deamido-NAD(+). |
- General function:
- Involved in hydrolase activity
- Specific function:
- Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of E.coli in stationary growth phase
- Gene Name:
- surE
- Uniprot ID:
- P0A840
- Molecular weight:
- 26900
Reactions
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
| A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
| (Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Nucleotidase that shows high phosphatase activity toward three nucleoside 5'-monophosphates, UMP, dUMP, and dTMP, and very low activity against TDP, IMP, UDP, GMP, dGMP, AMP, dAMP, and 6- phosphogluconate. Is strictly specific to substrates with 5'- phosphates and shows no activity against nucleoside 2'- or 3'- monophosphates. Might be involved in the pyrimidine nucleotide substrate cycles
- Gene Name:
- yjjG
- Uniprot ID:
- P0A8Y1
- Molecular weight:
- 25300
Reactions
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in DNA ligase (NAD+) activity
- Specific function:
- DNA ligase that catalyzes the formation of phosphodiester linkages between 5'-phosphoryl and 3'-hydroxyl groups in double-stranded DNA using NAD as a coenzyme and as the energy source for the reaction. It is essential for DNA replication and repair of damaged DNA
- Gene Name:
- ligA
- Uniprot ID:
- P15042
- Molecular weight:
- 73605
Reactions
| NAD(+) + (deoxyribonucleotide)(n) + (deoxyribonucleotide)(m) = AMP + beta-nicotinamide D-ribonucleotide + (deoxyribonucleotide)(n+m). |
- General function:
- Involved in nicotinate phosphoribosyltransferase activity
- Specific function:
- Nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate
- Gene Name:
- pncB
- Uniprot ID:
- P18133
- Molecular weight:
- 45897
Reactions
| Beta-nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in DNA ligase (NAD+) activity
- Specific function:
- Catalyzes the formation of phosphodiester linkages between 5'-phosphoryl and 3'-hydroxyl groups in double-stranded DNA using NAD as a coenzyme and as the energy source for the reaction
- Gene Name:
- ligB
- Uniprot ID:
- P25772
- Molecular weight:
- 63179
Reactions
| NAD(+) + (deoxyribonucleotide)(n) + (deoxyribonucleotide)(m) = AMP + beta-nicotinamide D-ribonucleotide + (deoxyribonucleotide)(n+m). |
- General function:
- Involved in negative regulation of transcription, DNA-dependent
- Specific function:
- NadR is bifunctional; it interacts with pnuC at low internal NAD levels, permitting transport of NMN intact into the cell. As NAD levels increase within the cell, the affinity of nadR for the operator regions of nadA, nadB, and pncB increases, repressing the transcription of these genes
- Gene Name:
- nadR
- Uniprot ID:
- P27278
- Molecular weight:
- 47346
Reactions
| ATP + nicotinamide ribonucleotide = diphosphate + NAD(+). |
| ATP + N-ribosylnicotinamide = ADP + nicotinamide ribonucleotide. |
- General function:
- Involved in catalytic activity
- Specific function:
- Involved in the catabolism of quinolinic acid (QA)
- Gene Name:
- nadC
- Uniprot ID:
- P30011
- Molecular weight:
- 32762
Reactions
| Beta-nicotinate D-ribonucleotide + diphosphate + CO(2) = pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- NAD(+) + H(2)O = AMP + NMN
- Gene Name:
- nudC
- Uniprot ID:
- P32664
- Molecular weight:
- 29689
Reactions
| NAD(+) + H(2)O = AMP + NMN. |
- General function:
- Involved in nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
- Specific function:
- Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6- dimethylbenzimidazole (DMB)
- Gene Name:
- cobT
- Uniprot ID:
- P36562
- Molecular weight:
- 36987
Reactions
| Beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole = nicotinate + alpha-ribazole 5'-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Nucleotidase that shows strict specificity toward deoxyribonucleoside 5'-monophosphates and does not dephosphorylate 5'-ribonucleotides or ribonucleoside 3'-monophosphates. Might be involved in the regulation of all dNTP pools in E.coli
- Gene Name:
- yfbR
- Uniprot ID:
- P76491
- Molecular weight:
- 22708
Reactions
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- pyridine nucleotide biosynthetic process
- Specific function:
- Has nicotinamidemononucleotide (NMN) aminohydrolase activity, not active on other substrates.
- Gene Name:
- pncC
- Uniprot ID:
- P0A6G3
- Molecular weight:
- 17581
Reactions
| Beta-nicotinamide D-ribonucleotide + H(2)O = beta-nicotinate D-ribonucleotide + NH(3) |
Transporters
- General function:
- Involved in transport
- Specific function:
- Required for nicotinamide riboside transport across the inner membrane
- Gene Name:
- pnuC
- Uniprot ID:
- P0AFK2
- Molecular weight:
- 26996
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368