WordNet

a salt of phosphoric acid (同)orthophosphate, inorganic_phosphate
carbonated drink with fruit syrup and a little phosphoric acid
(biochemistry) purine base found in DNA and RNA; pairs with thymine in DNA and with uracil in RNA (同)A

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〈U〉リン酸塩 / 《複数形で》リン酸肥料
アデニン(肝臓・茶の葉から採れる塩基の一種)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/08/05 19:48:38」(JST)

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Nicotinamide adenine dinucleotide phosphate, abbreviated NADP⁺ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent.

NADPH is the reduced form of NADP⁺. NADP⁺ differs from NAD⁺ in the presence of an additional phosphate group on the 2' position of the ribose ring that carries the adenine moiety.

In plants

In photosynthetic organisms, NADPH is produced by [[tripalamitin -NADP+ reductase|ferredoxin-NADP⁺ reductase]] in the last step of the electron chain of the light reactions of photosynthesis. It is used as reducing power for the biosynthetic reactions in the Calvin cycle to assimilate carbon dioxide. It is used to help turn the carbon dioxide into glucose. It is also needed in the reduction of nitrate into ammonia for plant assimilation in nitrogen cycle.

In animals

The major source of NADPH in animals and other non-photosynthetic organisms is the pentose phosphate pathway.

However, there are several other lesser-known mechanisms of generating NADPH, all of which depend on the presence of mitochondria. The key enzymes in these processes are: NADP-linked malic enzyme, NADP-linked isocitrate dehydrogenase, NADP-linked glutamate dehydrogenase and nicotinamide nucleotide transhydrogenase.^[1] The isocitrate dehydrogenase mechanism appears to be the major source of NADPH in fat and possibly also liver cells.^[2] Also, in mitochondria, NADH kinase produces NADPH and ADP, using NADH and ATP as substrates.

Function

NADPH provides the reducing equivalents for biosynthetic reactions and the oxidation-reduction involved in protecting against the toxicity of ROS (reactive oxygen species), allowing the regeneration of GSH (reduced glutathione).^[3] NADPH is also used for anabolic pathways, such as lipid synthesis, cholesterol synthesis, and fatty acid chain elongation.

The NADPH system is also responsible for generating free radicals in immune cells. These radicals are used to destroy pathogens in a process termed the respiratory burst.^[4] It is the source of reducing equivalents for cytochrome P450 hydroxylation of aromatic compounds, steroids, alcohols, and drugs.

Ball-and-stick models of NADP+ and NADPH

NADP+

NADPH

References

^ Hanukoglu I, Rapoport R (Feb–May 1995). "Routes and regulation of NADPH production in steroidogenic mitochondria". Endocrine Research 21 (1-2): 231–41. doi:10.3109/07435809509030439. PMID 7588385.
^ Palmer, Michael. "10.4.3 Supply of NADPH for fatty acid synthesis". Metabolism Course Notes. Retrieved 6 April 2012.
^ Rush, Glenn F.; Gorski, Joel R.; Ripple, Mary G.; Sowinski, Janice; Bugelski, Peter; Hewitt, William R. (May 1985). "Organic hydroperoxide-induced lipid peroxidation and cell death in isolated hepatocytes". Toxicology and Applied Pharmacology 78 (3): 473–483. doi:10.1016/0041-008X(85)90255-8. PMID 4049396.
^ Ogawa K, Suzuki K, Okutsu M, Yamazaki K, Shinkai S (2008). "The association of elevated reactive oxygen species levels from neutrophils with low-grade inflammation in the elderly". Immunity & Ageing 5: 13. doi:10.1186/1742-4933-5-13. PMC 2582223. PMID 18950479.

UpToDate Contents

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1. 慢性肉芽腫性疾患：病因、臨床症状、および診断 chronic granulomatous disease pathogenesis clinical manifestations and diagnosis
2. メトヘモグロビン血症の遺伝学および病因 genetics and pathogenesis of methemoglobinemia
3. まれな先天性副腎過形成 uncommon congenital adrenal hyperplasias
4. 免疫不全症を引き起こすミエロペルオキシダーゼ欠損症および酵素白血球欠損症 myeloperoxidase deficiency and other enzymatic wbc defects causing immunodeficiency
5. グルコース-6-リン酸脱水素酵素欠損症の遺伝学および病態生理 genetics and pathophysiology of glucose 6 phosphate dehydrogenase deficiency

English Journal

Association of the p22phox polymorphism C242T with the risk of late-onset Alzheimer's disease in a northern Han Chinese population.

Fu Q1, Qi F1, Tian F1, Ma G2, Che F1, Du Y3, Gao N1.
The International journal of neuroscience.Int J Neurosci.2016 Jul;126(7):637-40. doi: 10.3109/00207454.2015.1052877. Epub 2015 Aug 17.
The C242T polymorphism of the CYBA gene that encodes p22phox, a component of nicotinamide adenine dinucleotide phosphate oxidase, has been found to modulate reactive oxygen species (ROS) production. Oxidative stress is thought to play a pivotal role in the pathophysiology of Alzheimer's disease (AD)
PMID 26000926

A hydrophilic interaction liquid chromatography-mass spectrometry (HILIC-MS) based metabolomics study on colour stability of ovine meat.

Subbaraj AK1, Kim YH2, Fraser K3, Farouk MM4.
Meat science.Meat Sci.2016 Jul;117:163-72. doi: 10.1016/j.meatsci.2016.02.028. Epub 2016 Feb 20.
Meat colour is one of the cues available to the consumer to gauge overall meat quality and wholesomeness. Colour stability of meat is determined by several factors both inherent to the animal and post-slaughter conditions, including ageing, storage/packaging and display times. A hydrophilic interact
PMID 26986230

Data supporting the absence of FNR dynamic photosynthetic membrane recruitment in trol mutants.

Vojta L1, Fulgosi H1.
Data in brief.Data Brief.2016 Feb 26;7:393-6. doi: 10.1016/j.dib.2016.02.044. eCollection 2016.
In photosynthesis, the flavoenzyme ferredoxin:NADP(+) oxidoreductase (FNR) catalyses the final electron transfer from ferredoxin to NADP(+), which is considered as the main pathway of high-energy electron partitioning in chloroplasts (DOI: 10.1111/j.1365-313X.2009.03999.x[1], DOI: 10.1038/srep10085[
PMID 26977444

Japanese Journal

Mitochondrial reactive oxygen species accelerate gastric cancer cell invasion

Tamura Masato,Matsui Hirofumi,Tomita Tsutomu,Sadakata Hisato,Indo Hiroko P.,Majima Hideyuki J.,Kaneko Tsuyoshi,Hyodo Ichinosuke
Journal of Clinical Biochemistry and Nutrition 54(1), 12-17, 2014
… The relation between reactive oxygen species and tumor invasion is mainly reported that nicotinamide adenine dinucleotide phosphate oxidase in the cell membrane is a reactive oxygen species producer for formulating an invadopodia. …
NAID 130004466736

Production of Reactive Oxygen Species in the Diabetic Heart:– Roles of Mitochondria and NADPH Oxidase –

Teshima Yasushi,Takahashi Naohiko,Nishio Satoru,Saito Shotaro,Kondo Hidekazu,Fukui Akira,Aoki Kouhei,Yufu Kunio,Nakagawa Mikiko,Saikawa Tetsunori
Circulation Journal 78(2), 300-306, 2014
… Emerging evidence shows that mitochondria and nicotinamide adenine dinucleotide phosphate (NADPH) oxidase are dominant mechanisms of ROS production in the diabetic heart. …
NAID 130003382238

G6PT Inhibition Model Using HL-60 Cells and Induction of ROS Production through PKC/NOX2 Activation : Clinical Condition for Elucidation of Glycogen Storage Disease Type Ⅰb

Satoh Daisuke,Ohte Mariko,Maeda Tohru [他],Nakamura Katsunori,Matsunaga Tamihide
Biological and Pharmaceutical Bulletin 37(4), 534-540, 2014
… Glycogen storage disease type Ib (GSD-Ib) is caused by mutations in the glucose-6-phosphate transporter (G6PT) gene, which is involved in glycogen metabolism. …
NAID 130003382133

Related Pictures

★リンクテーブル★

リンク元	「NADPH」「ニコチンアミドアデニンジヌクレオチドリン酸」「NADP」「NADP+」
関連記事	「phosphate」「nicotinamide」

「NADPH」

Nicotinamide adenine dinucleotide phosphate
Identifiers
CAS Number	53-59-8
ChEBI	CHEBI:44409
ChEMBL	ChEMBL213053
ChemSpider	5674
Jmol 3D model	Interactive image
MeSH	NADP
PubChem	5885
	InChI InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1 Key: XJLXINKUBYWONI-NNYOXOHSSA-N ; InChI=1/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1 Key: XJLXINKUBYWONI-NNYOXOHSBN ;
	SMILES O=C(N)c1ccc[n+](c1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP([O-])(=O)OP(=O)(O)OC[C@H]5O[C@@H](n4cnc3c(ncnc34)N)[C@H](OP(=O)(O)O)[C@@H]5O ;
Properties
Chemical formula	C21H29N7O17P3
Molar mass	744.42 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

関: nicotinamide adenine dinucleotide phosphate

グルタチオンの還元に必要。
足らなくなると、フリーラジカルや過酸化物を無毒化できなくなる。
赤血球の場合でNADPHが足らないと、fava beans, sulfonamides, primaquineおよび抗結核薬などの酸化剤によって溶血性貧血を起こす。

「ニコチンアミドアデニンジヌクレオチドリン酸」

　　[★]

英: nicotinamide adenine dinucleotide phosphate NADP
同: NADP+、トリホスホピリジンヌクレオチド triphosphopyridine nucleotide TPN
関: NADPH

「NADP」

　　[★] ニコチンアミドアデニンジヌクレオチドリン酸 nicotinamide adenine dinucleotide phosphate

「NADP+」