| Identification |
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| YMDB ID | YMDB00193 |
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| Name | Nicotinic acid mononucleotide |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Nicotinic acid mononucleotide, also known as beta-nicotinate D-ribonucleotide or deamido-NMN, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Nicotinic acid mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinic acid mononucleotide exists in all eukaryotes, ranging from yeast to humans. Within yeast, nicotinic acid mononucleotide participates in a number of enzymatic reactions. In particular, nicotinic acid mononucleotide can be biosynthesized from quinolinic acid and phosphoribosyl pyrophosphate through its interaction with the enzyme nicotinate-nucleotide pyrophosphorylase [carboxylating]. In addition, nicotinic acid mononucleotide can be converted into nicotinic acid adenine dinucleotide through the action of the enzyme nicotinamide/nicotinic acid mononucleotide adenylyltransferase. In yeast, nicotinic acid mononucleotide is involved in the metabolic pathway called the nad metabolism pathway. |
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| Structure | |
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| Synonyms | - 3-carboxy-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt
- 3-carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)-Pyridinium inner salt
- 3-carboxy-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt
- 3-Carboxy-1-beta-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
- 3-Carboxy-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
- 3-Pyridinecarboxylic acid mononucleotide
- Beta-nicotinate D-ribonucleotide
- beta-Nicotinic acid mononucleotide
- Deamido nicotinamide ribonucleotide
- deamido-nicotinamide mononucleotide
- Deamido-NMN
- NaMN
- Nicotinate D-ribonucleoside
- Nicotinate D-ribonucleotide
- Nicotinate mononucleotide
- nicotinate nucleotide
- nicotinate ribonucleotide
- nicotinate-D-ribonucleotide
- nicotinate-delta-ribonucleotide
- Nicotinic acid mononucleotide
- Nicotinic acid ribonucleotide
- Nicotinic acid ribotide
- Nicotinic mononucleotide
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| CAS number | 321-02-8 |
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| Weight | Average: 337.2198
Monoisotopic: 337.056267627 |
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| InChI Key | OGCWVIVNTBZPBW-BHRXDNSCSA-N |
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| InChI | InChI=1S/C11H16NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-3,6-10,13-14H,4-5H2,(H2-,15,16,17,18,19)/t6?,7-,8-,9-,10-/m1/s1 |
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| IUPAC Name | 3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium |
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| Traditional IUPAC Name | 3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium |
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| Chemical Formula | C11H16NO9P |
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| SMILES | [H]OC(=O)C1([H])C([H])=C([H])C([H])=[N+](C1([H])[H])[C@]1([H])O[C@]([H])(C([H])([H])OP([O-])(=O)O[H])[C@@]([H])(O[H])[C@@]1([H])O[H] |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Pentose phosphates |
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| Alternative Parents | |
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| Substituents | - Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Tetrahydrofuran
- 1,2-diol
- Secondary alcohol
- Organic 1,3-dipolar compound
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Oxacycle
- Organoheterocyclic compound
- Propargyl-type 1,3-dipolar organic compound
- Carbonyl group
- Organic oxide
- Organonitrogen compound
- Hydrocarbon derivative
- Organic zwitterion
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Solid |
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| Charge | 0 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | |
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | |
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| KEGG Pathways | | Nicotinate and nicotinamide metabolism | ec00760 |  |
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| SMPDB Reactions | |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra | |
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| References |
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| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- de Figueiredo, L. F., Gossmann, T. I., Ziegler, M., Schuster, S. (2011). "Pathway Analysis of NAD+ metabolism." Biochem J :.21729004
- Lu, S. P., Lin, S. J. (2011). "Phosphate-responsive signaling pathway is a novel component of NAD+ metabolism in Saccharomyces cerevisiae." J Biol Chem 286:14271-14281.21349851
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| Synthesis Reference: | Not Available |
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| External Links: | |
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