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1094-61-7 | β-Nicotinamide mononucleotide
CAS No: 1094-61-7 Catalog No: AG003880 MDL No:MFCD00038748
Product Description
Catalog Number:
AG003880
Chemical Name:
β-Nicotinamide mononucleotide
CAS Number:
1094-61-7
Molecular Formula:
C11H15N2O8P
Molecular Weight:
334.2192
MDL Number:
MFCD00038748
IUPAC Name:
[(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
InChI:
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 Key:
DAYLJWODMCOQEW-TURQNECASA-N
SMILES:
O[C@@H]1[C@H](O)[C@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(O)[O-]
EC Number:
214-136-5
UNII:
2KG6QX4W0V
Properties
Complexity:
455
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
334.057g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
334.221g/mol
Monoisotopic Mass:
334.057g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
166A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.5
Literature
| Title | Journal |
|---|---|
| Oxyresveratrol stimulates mucin production in an NAD(+)-dependent manner in human intestinal goblet cells. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20180801 |
| METALLOPROTEINS. A tethered niacin-derived pincer complex with a nickel-carbon bond in lactate racemase. | Science (New York, N.Y.) 20150703 |
| A high-fat diet and NAD(+) activate Sirt1 to rescue premature aging in cockayne syndrome. | Cell metabolism 20141104 |
| Elevated microRNA-34a in obesity reduces NAD+ levels and SIRT1 activity by directly targeting NAMPT. | Aging cell 20131201 |
| Resistin impairs SIRT1 function and induces senescence-associated phenotype in hepatocytes. | Molecular and cellular endocrinology 20130905 |
| A urinary metabonomics study on biochemical changes in yeast-induced pyrexia rats: a new approach to elucidating the biochemical basis of the febrile response. | Chemico-biological interactions 20130625 |
| Comparison of the formation of nicotinic acid conjugates in leaves of different plant species. | Plant physiology and biochemistry : PPB 20121101 |
| Induced fit and the catalytic mechanism of isocitrate dehydrogenase. | Biochemistry 20120911 |
| Molecular determinants of ligand selectivity for the human multidrug and toxin extruder proteins MATE1 and MATE2-K. | The Journal of pharmacology and experimental therapeutics 20120601 |
| Enzymatic biofuel cells utilizing a biomimetic cofactor. | Chemical communications (Cambridge, England) 20120211 |
| Characterization of human nicotinate phosphoribosyltransferase: Kinetic studies, structure prediction and functional analysis by site-directed mutagenesis. | Biochimie 20120201 |
| Effects of long-acting somatostatin analogues on adrenal growth and phosphoribosyl pyrophosphate formation in experimental diabetes. | International journal of experimental pathology 20120201 |
| Catalysis-based inhibitors of the calcium signaling function of CD38. | Biochemistry 20120110 |
| The high-resolution crystal structure of periplasmic Haemophilus influenzae NAD nucleotidase reveals a novel enzymatic function of human CD73 related to NAD metabolism. | The Biochemical journal 20120101 |
| Identification of mitochondrial electron transport chain-mediated NADH radical formation by EPR spin-trapping techniques. | Biochemistry 20111220 |
| Nicotinamide mononucleotide protects against pro-inflammatory cytokine-mediated impairment of mouse islet function. | Diabetologia 20111201 |
| Nicotinamide mononucleotide, a key NAD(+) intermediate, treats the pathophysiology of diet- and age-induced diabetes in mice. | Cell metabolism 20111005 |
| Mitochondria-localized NAD biosynthesis by nicotinamide mononucleotide adenylyltransferase in Jerusalem artichoke (Helianthus tuberosus L.) heterotrophic tissues. | Planta 20111001 |
| Effect of nicotinamide mononucleotide on insulin secretion and gene expressions of PDX-1 and FoxO1 in RIN-m5f cells. | Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences 20111001 |
| ArsAB, a novel enzyme from Sporomusa ovata activates phenolic bases for adenosylcobamide biosynthesis. | Molecular microbiology 20110801 |
| A fluorometric assay for high-throughput screening targeting nicotinamide phosphoribosyltransferase. | Analytical biochemistry 20110501 |
| Comparative genomics of NAD(P) biosynthesis and novel antibiotic drug targets. | Journal of cellular physiology 20110201 |
| Wld(S) reduces paraquat-induced cytotoxicity via SIRT1 in non-neuronal cells by attenuating the depletion of NAD. | PloS one 20110101 |
| Nicotinamide phosphoribosyltransferase/visfatin does not catalyze nicotinamide mononucleotide formation in blood plasma. | PloS one 20110101 |
| Recognition of nucleoside monophosphate substrates by Haemophilus influenzae class C acid phosphatase. | Journal of molecular biology 20101210 |
| A possibility of nutriceuticals as an anti-aging intervention: activation of sirtuins by promoting mammalian NAD biosynthesis. | Pharmacological research 20100701 |
| Visualization and quantification of NAD(H) in brain sections by a novel histo-enzymatic nitrotetrazolium blue staining technique. | Brain research 20100226 |
| Identification of Isn1 and Sdt1 as glucose- and vitamin-regulated nicotinamide mononucleotide and nicotinic acid mononucleotide [corrected] 5'-nucleotidases responsible for production of nicotinamide riboside and nicotinic acid riboside. | The Journal of biological chemistry 20091211 |
| Detection and pharmacological modulation of nicotinamide mononucleotide (NMN) in vitro and in vivo. | Biochemical pharmacology 20090515 |
| Tailoring RNA modular units on a common scaffold: a modular ribozyme with a catalytic unit for beta-nicotinamide mononucleotide-activated RNA ligation. | RNA (New York, N.Y.) 20090501 |
| Mechanism-based small molecule probes for labeling CD38 on live cells. | Journal of the American Chemical Society 20090211 |
| Perivascular adipose tissue-derived visfatin is a vascular smooth muscle cell growth factor: role of nicotinamide mononucleotide. | Cardiovascular research 20090201 |
| Extracellular Nampt promotes macrophage survival via a nonenzymatic interleukin-6/STAT3 signaling mechanism. | The Journal of biological chemistry 20081212 |
| Theoretical studies of the quinolinic acid to nicotinic acid mononucleotide transformation. | The Journal of organic chemistry 20081205 |
| Visfatin: a new player in mesangial cell physiology and diabetic nephropathy. | American journal of physiology. Renal physiology 20081101 |
| Weak coupling of ATP hydrolysis to the chemical equilibrium of human nicotinamide phosphoribosyltransferase. | Biochemistry 20081021 |
| Covalent and noncovalent intermediates of an NAD utilizing enzyme, human CD38. | Chemistry & biology 20081020 |
| Biosynthesis of trigonelline from nicotinate mononucleotide in mungbean seedlings. | Phytochemistry 20080101 |
| Age-associated loss of Sirt1-mediated enhancement of glucose-stimulated insulin secretion in beta cell-specific Sirt1-overexpressing (BESTO) mice. | Aging cell 20080101 |
| Nampt/PBEF/Visfatin regulates insulin secretion in beta cells as a systemic NAD biosynthetic enzyme. | Cell metabolism 20071101 |
| Crystal structure of human nicotinamide riboside kinase. | Structure (London, England : 1993) 20070801 |
| Nicotinamidase participates in the salvage pathway of NAD biosynthesis in Arabidopsis. | The Plant journal : for cell and molecular biology 20070301 |
| Arabidopsis thaliana nicotinate/nicotinamide mononucleotide adenyltransferase (AtNMNAT) is required for pollen tube growth. | The Plant journal : for cell and molecular biology 20070201 |
| Crystal structure of visfatin/pre-B cell colony-enhancing factor 1/nicotinamide phosphoribosyltransferase, free and in complex with the anti-cancer agent FK-866. | Journal of molecular biology 20060908 |
| Probing hot spots at protein-ligand binding sites: a fragment-based approach using biophysical methods. | Journal of medicinal chemistry 20060810 |
| The simultaneous measurement of nicotinamide adenine dinucleotide and related compounds by liquid chromatography/electrospray ionization tandem mass spectrometry. | Analytical biochemistry 20060515 |
| Crystal structure of quinolinic acid phosphoribosyltransferase from Helicobacter pylori. | Proteins 20060401 |
| The first crystal structure of a thioacylenzyme intermediate in the ALDH family: new coenzyme conformation and relevance to catalysis. | Biochemistry 20060307 |
| NAD(P) synthesis and pyridine nucleotide cycling in plants and their potential importance in stress conditions. | Journal of experimental botany 20060101 |
| Construction of an artificial ribozyme which ligates an RNA fragment activated by nicotinamide mononucleotide. | Nucleic acids symposium series (2004) 20060101 |
| NAD-, NMN-, and NADP-dependent modification of dinitrogenase reductases from Rhodospirillum rubrum and Azotobacter vinelandii. | FEBS letters 20051024 |
| Interactions between melatonin and nicotinamide nucleotide: NADH preservation in cells and in cell-free systems by melatonin. | Journal of pineal research 20050901 |
| NAD deamidation 'a new reaction' by an enzyme from Aspergillus terreus DSM 826. | Antonie van Leeuwenhoek 20050201 |
| NAD+ specificity of bacterial DNA ligase revealed. | Structure (London, England : 1993) 20040801 |
| Structural rearrangement accompanying NAD+ synthesis within a bacterial DNA ligase crystal. | Structure (London, England : 1993) 20040801 |
| Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans. | Cell 20040514 |
| Structure and function of nicotinamide mononucleotide adenylyltransferase. | Current medicinal chemistry 20040401 |
| ADP-ribosyl cyclase; crystal structures reveal a covalent intermediate. | Structure (London, England : 1993) 20040301 |
| Effects of hydrogen peroxide upon nicotinamide nucleotide metabolism in Escherichia coli: changes in enzyme levels and nicotinamide nucleotide pools and studies of the oxidation of NAD(P)H by Fe(III). | The Journal of biological chemistry 20031024 |
| Porin OmpP2 of Haemophilus influenzae shows specificity for nicotinamide-derived nucleotide substrates. | The Journal of biological chemistry 20030704 |
| Crystallization and preliminary X-ray crystallographic analysis of quinolinate phosphoribosyltransferase of Helicobacter pylori. | Acta crystallographica. Section D, Biological crystallography 20030701 |
| Identification and characterization of a second NMN adenylyltransferase gene in Saccharomyces cerevisiae. | Protein expression and purification 20030201 |
| Crystal structure and site-directed mutagenesis of enzymatic components from Clostridium perfringens iota-toxin. | Journal of molecular biology 20030117 |
| Substrate specificity of mammalian pyridine nucleotide transglycosidases. | Journal of nutritional science and vitaminology 20020601 |
| Synthesis of pyridine nucleotide analogs consisting of nicotinoylamino acids by means of transglycosidation reactions catalyzed by mammalian pyridine nucleotide transglycosidases. | Journal of nutritional science and vitaminology 20020601 |
| Crystal structure of human nicotinamide mononucleotide adenylyltransferase in complex with NMN. | FEBS letters 20020410 |
| Crystallographic studies on human BST-1/CD157 with ADP-ribosyl cyclase and NAD glycohydrolase activities. | Journal of molecular biology 20020222 |
| Purification and structure of the major product obtained by reaction of NADPH and NMNH with the myeloperoxidase/hydrogen peroxide/chloride system. | European journal of biochemistry 20010501 |
| A disubstituted NAD+ analogue is a nanomolar inhibitor of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. | Bioorganic & medicinal chemistry letters 20010122 |
| Mechanism and activation for allosteric adenosine 5'-monophosphate nucleosidase. Kinetic alpha-deuterium isotope effects for the enzyme-catalyzed hydrolysis of adenosine 5'-monophosphate and nicotinamide mononucleotide. | The Journal of biological chemistry 19860405 |
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