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Nicotinamide mononucleotide
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Names |
IUPAC name
3-Carbamoyl-1-[5-O-(hydroxyphosphinato)-β-D-ribofuranosyl]pyridinium
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Other names
- Nicotinamide ribonucleoside 5'-phosphate
- Nicotinamide D-ribonucleotide
- β-Nicotinamide ribose monophosphate
- Nicotinamide nucleotide
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Identifiers |
CAS Number
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3D model (JSmol)
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ChemSpider |
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InChI
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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
Key: DAYLJWODMCOQEW-TURQNECASA-N
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SMILES
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c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)[O-])O)O)C(=O)N
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Properties |
Chemical formula
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C11H15N2O8P |
Molar mass |
334.22 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references |
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Nicotinamide mononucleotide ("NMN" and "β-NMN") is a nucleotide derived from ribose and nicotinamide.[1] Like nicotinamide riboside, NMN is a derivative of niacin, and humans have enzymes that can use NMN to generate nicotinamide adenine dinucleotide (NADH).[1]
Because NADH is a cofactor for processes inside mitochondria, for sirtuins, and for PARP, NMN has been studied and hyped as a potential neuroprotective and anti-aging agent.[2][3]
References
- ^ a b Bogan, KL; Brenner, C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annual review of nutrition. 28: 115–30. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.
- ^ Brazill, JM; Li, C; Zhu, Y; Zhai, RG (June 2017). "NMNAT: It's an NAD+ synthase… It's a chaperone… It's a neuroprotector". Current Opinion in Genetics & Development. 44: 156–162. doi:10.1016/j.gde.2017.03.014. PMID 28445802.
- ^ Stipp, David (March 11, 2015). "Beyond Resveratrol: The Anti-Aging NAD Fad". Scientific American Blog Network.
UpToDate Contents
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English Journal
- Differential responses of B vitamins in black soybean seeds.
- Kim GP1, Lee J2, Ahn KG1, Hwang YS1, Choi Y3, Chun J4, Chang WS5, Choung MG6.Author information 1Department of Herbal Medicine Resource, Dogye Campus, Kangwon National University, Hwangjori #3, Dogye-up, Samcheok 245-907, Republic of Korea.2USDA-ARS, Tree Fruit Research Laboratory, 1104 N. Western Ave., Wenatchee, WA 98801, USA.3Functional Food and Nutrition Division, National Academy of Agricultural Sciences, Rural Development Administration, Suwon 441-853, Republic of Korea.4Department of Food Science and Technology, Sunchon National University, Sunchon 540-742, Republic of Korea.5Department of Biology, University of Texas-Arlington, Arlington, TX 76019, USA.6Department of Herbal Medicine Resource, Dogye Campus, Kangwon National University, Hwangjori #3, Dogye-up, Samcheok 245-907, Republic of Korea; Department of Biology, University of Texas-Arlington, Arlington, TX 76019, USA. Electronic address: cmg7004@kangwon.ac.kr.AbstractThis study was aimed to determine the contents and the association of B vitamins from seeds of 10 black and one yellow soybean (Glycine max (L.) Merr.) varieties with either green or yellow cotyledon. Thiamine, flavin adenine dinucleotide (FAD), riboflavin and total riboflavin were found highest in 'Chengjakong', while flavin mononucleotide (FMN) was greatest in 'Mirang'. Nicotinic acid and total vitamin B3 were highest in 'Shingi' as a yellow soybean variety but pantothenic acid and pyridoxine contents were greatest in 'Tawon' and 'Mirang', respectively. These content variations of B vitamins directly reflected the wide segregation of soybean varieties on the principal component analysis (PCA) scores plot, indicating that these 4 soybean varieties appeared to be least associated with other soybean varieties based on the different responses of B vitamins. The results of cluster and correlation analyses presented that the cotyledon colour of soybean seed contributed to a variation of B vitamin contents. Overall, the results suggest that a wide range of B vitamin contents would be affected by genotypic factors alongside the difference of cotyledon colour.
- Food chemistry.Food Chem.2014 Jun 15;153:101-8. doi: 10.1016/j.foodchem.2013.12.047. Epub 2013 Dec 14.
- This study was aimed to determine the contents and the association of B vitamins from seeds of 10 black and one yellow soybean (Glycine max (L.) Merr.) varieties with either green or yellow cotyledon. Thiamine, flavin adenine dinucleotide (FAD), riboflavin and total riboflavin were found highest in
- PMID 24491706
- Deficiency of Nicotinamide Mononucleotide Adenylyltransferase 3 (Nmnat3) Causes Hemolytic Anemia by Altering the Glycolytic Flow in Mature Erythrocytes.
- Hikosaka K1, Ikutani M, Shito M, Kazuma K, Gulshan M, Nagai Y, Takatsu K, Konno K, Tobe K, Kanno H, Nakagawa T.Author information 1University of Toyama, Japan;AbstractNAD biosynthesis is of substantial interest owing to its important roles in regulating various biological processes. Nicotinamide mononucleotide adenylyltransferase 3 (Nmnat3) is considered a mitochondria- localized NAD synthesis enzyme involved in de novo and salvage pathways. Although the biochemical properties of Nmnat3 are well documented, its physiological function in vivo remains unclear. In this study, we demonstrated that Nmnat3 was localized in the cytoplasm of mature erythrocytes and critically regulated their NAD pool. Deficiency of Nmnat3 in mice caused splenomegaly and hemolytic anemia, which was associated with the findings that Nmnat3-deficient erythrocytes had markedly lower ATP levels and shortened lifespans. However, NAD level in other tissues were not apparently affected by the deficiency of Nmnat3. LC-MS/MS based metabolomics revealed that the glycolysis pathway in Nmnat3-deficient erythrocytes was blocked at glyceraldehyde 3-phosphate dehydrogenase (GAPDH) step because of the shortage of co-enzyme NAD. Stable isotope tracer analysis further demonstrated that deficiency of Nmnat3 resulted in glycolysis stall and a shift to pentose phosphate pathway. Our findings indicate the critical roles of Nmnat3 in maintenance of the NAD pool in mature erythrocytes and the physiological impacts at its absence in mice.
- The Journal of biological chemistry.J Biol Chem.2014 Apr 16. [Epub ahead of print]
- NAD biosynthesis is of substantial interest owing to its important roles in regulating various biological processes. Nicotinamide mononucleotide adenylyltransferase 3 (Nmnat3) is considered a mitochondria- localized NAD synthesis enzyme involved in de novo and salvage pathways. Although the biochemi
- PMID 24739386
- The NAD(+) synthesizing enzyme nicotinamide mononucleotide adenylyltransferase 2 (NMNAT-2) is a p53 downstream target.
- Pan LZ1, Ahn DG1, Sharif T1, Clements D2, Gujar SA3, Lee PW4.Author information 1Department of Microbiology and Immunology; Dalhousie University; Halifax, Nova Scotia, Canada.2Department of Pathology; Dalhousie University; Halifax, Nova Scotia, Canada.3Department of Microbiology and Immunology; Dalhousie University; Halifax, Nova Scotia, Canada; Strategy & Organizational Performance; IWK Health Centre; Halifax, Nova Scotia, Canada.4Department of Microbiology and Immunology; Dalhousie University; Halifax, Nova Scotia, Canada; Department of Pathology; Dalhousie University; Halifax, Nova Scotia, Canada.AbstractNAD(+) metabolism plays key roles not only in energy production but also in diverse cellular physiology. Aberrant NAD(+) metabolism is considered a hallmark of cancer. Recently, the tumor suppressor p53, a major player in cancer signaling pathways, has been implicated as an important regulator of cellular metabolism. This notion led us to examine whether p53 can regulate NAD(+) biosynthesis in the cell. Our search resulted in the identification of nicotinamide mononucleotide adenylyltransferase 2 (NMNAT-2), a NAD(+) synthetase, as a novel downstream target gene of p53. We show that NMNAT-2 expression is induced upon DNA damage in a p53-dependent manner. Two putative p53 binding sites were identified within the human NMNAT-2 gene, and both were found to be functional in a p53-dependent manner. Furthermore, knockdown of NMNAT-2 significantly reduces cellular NAD(+) levels and protects cells from p53-dependent cell death upon DNA damage, suggesting an important functional role of NMNAT-2 in p53-mediated signaling. Our demonstration that p53 modulates cellular NAD(+) synthesis is congruent with p53's emerging role as a key regulator of metabolism and related cell fate.
- Cell cycle (Georgetown, Tex.).Cell Cycle.2014 Mar 15;13(6):1041-8. doi: 10.4161/cc.28128. Epub 2014 Feb 7.
- NAD(+) metabolism plays key roles not only in energy production but also in diverse cellular physiology. Aberrant NAD(+) metabolism is considered a hallmark of cancer. Recently, the tumor suppressor p53, a major player in cancer signaling pathways, has been implicated as an important regulator of ce
- PMID 24552824
Japanese Journal
- 糖尿病治療標的としてのNAD依存性脱アセチル化酵素SIRT1とNAD合成系 (内分泌) -- (基礎分野での進歩)
- 1G09-1 出芽酵母Saccharomyces cerevisiaeにおける新規なNAD生合成系路(生合成・天然物化学,一般講演)
- Protection of vincristine-induced neuropathy by WldS expression and the independence of the activity of Nmnat1
- Watanabe Masashi,Tsukiyama Tadasuke,Hatakeyama Shigetsugu
- Neuroscience Letters 411(3), 228-232, 2007-01-16
- … The slow Wallerian degeneration protein (WldS), a fusion protein containing amino-terminal E4B and full-length nicotinamide mononucleotide adenylyltransferase 1 (Nmnat1), delays axon degeneration caused by physical damages, toxins and genetic mutations which result in patients being diagnosed with neurodegenerative diseases. …
- NAID 120000969949
Related Links
- Nicotinamide mononucleotide - Medical Terms is a service who provides descriptions and explanations of health related terms ... Information provided on this site is intended for informational and educational purposes only. It is not ...
- Buy β-Nicotinamide mononucleotide (CAS 1094-61-7), a product of the eNAMPT reaction and a NAD+ intermediate, from Santa Cruz. Purity: ≥95%, MW: 334.22 ... β-Nicotinamide mononucleotide is a product of the extracellular ...
★リンクテーブル★
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- 英
- nicotinamide mononucleotide NMN
- 同
- ニコチンアミドリボヌクレオチド
- 関
- ニコチンアミドアデニンジヌクレオチド NAD、ニコチンアミド
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ニコチンアミド、ニコチン酸アミド