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Nicotinamide adenine dinucleotide phosphate information


Nicotinamide adenine dinucleotide phosphate
Identifiers
CAS Number
  • 53-59-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:44409 checkY
ChEMBL
  • ChEMBL2364573 ☒N
ChemSpider
  • 5674 checkY
ECHA InfoCard 100.000.163 Edit this at Wikidata
MeSH NADP
PubChem CID
  • 5885
UNII
  • BY8P107XEP checkY
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 checkY
    Key: XJLXINKUBYWONI-NNYOXOHSSA-N checkY
  • 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]2[C@H](O)[C@H](O)[C@H](O2)COP([O-])(=O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c4ncnc5N)[C@@H]([C@@H]3O)OP(=O)(O)O
Properties
Chemical formula
C21H29N7O17P3
Molar mass 744.416 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Nicotinamide adenine dinucleotide phosphate, abbreviated NADP+ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NADPH as a reducing agent ('hydrogen source'). NADPH is the reduced form, whereas NADP+ is the oxidized form. NADP+ is used by all forms of cellular life.[1]

NADP+ differs from NAD+ by the presence of an additional phosphate group on the 2' position of the ribose ring that carries the adenine moiety. This extra phosphate is added by NAD+ kinase and removed by NADP+ phosphatase.[2]

  1. ^ Spaans SK, Weusthuis RA, van der Oost J, Kengen SW (2015). "NADPH-generating systems in bacteria and archaea". Frontiers in Microbiology. 6: 742. doi:10.3389/fmicb.2015.00742. PMC 4518329. PMID 26284036.
  2. ^ Kawai S, Murata K (April 2008). "Structure and function of NAD kinase and NADP phosphatase: key enzymes that regulate the intracellular balance of NAD(H) and NADP(H)". Bioscience, Biotechnology, and Biochemistry. 72 (4): 919–30. doi:10.1271/bbb.70738. PMID 18391451.

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Nicotinic acid adenine dinucleotide phosphate (NAADP) is a Ca2+-mobilizing second messenger synthesised in response to extracellular stimuli. Like its...

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derivative nicotinamide (niacinamide) is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+)...

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amide nicotinamide (niacinamide) is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+)...

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Adenine

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adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions...

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Flavin adenine dinucleotide

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In biochemistry, flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic...

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Dehydrogenase

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NAD+, or nicotinamide adenine dinucleotide, is a dinucleotide, containing two nucleotides. One of the nucleotides it contains is an adenine group, while...

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Photosynthesis

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molecules that participate in energetic processes: reduced nicotinamide adenine dinucleotide phosphate (NADPH) and ATP. In plants, algae, and cyanobacteria...

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Nicotinamide mononucleotide

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and niacin. In humans, several enzymes use NMN to generate nicotinamide adenine dinucleotide (NADH). In mice, it has been proposed that NMN is absorbed...

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acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor. The shikimate pathway is a seven-step...

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NADPH oxidase

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NADPH oxidase (nicotinamide adenine dinucleotide phosphate oxidase) is a membrane-bound enzyme complex that faces the extracellular space. It can be found...

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Biomolecule

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reactions (coenzyme A, flavin adenine dinucleotide, flavin mononucleotide, and nicotinamide adenine dinucleotide phosphate). DNA structure is dominated...

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also fructose 6-phosphate are an intermediate of the pentose-phosphate pathway which generates nicotinamide adenine dinucleotide phosphate (NADPH) and pentoses...

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B vitamins

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certain conditions. Vitamin B4: can refer to the distinct chemicals choline, adenine, or carnitine. Choline is synthesized by the human body, but not sufficiently...

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Ribose

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For example, nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD), and nicotinamide adenine dinucleotide phosphate (NADP) all contain...

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Ferroptosis

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that regulate cysteine exploitation, glutathione state, nicotinamide adenine dinucleotide phosphate (NADP) function, lipid peroxidation, and iron homeostasis...

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Menthol

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(−)-Limonene-3-hydroxylase (L3OH), using O2 and then nicotinamide adenine dinucleotide phosphate (NADPH) catalyzes the allylic hydroxylation of (−)-limonene...

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Autoimmunity

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as well. CGD is a caused by decreased production of nicotinamide adenine dinucleotide phosphate (NADPH) oxidase by neutrophils. Hypomorphic RAG mutations...

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Transaldolase

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pathway has two metabolic functions: (1) generation of nicotinamide adenine dinucleotide phosphate (reduced NADPH), for reductive biosynthesis, and (2)...

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AKR1B1

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encoded by the AKR1B1 gene in humans. It is a reduced nicotinamide-adenine dinucleotide phosphate (NADPH)-dependent enzyme catalyzing the reduction of...

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