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Nicotinic acid adenine dinucleotide phosphate information


Nicotinic acid adenine dinucleotide phosphate
Ball-and-stick model of the NAADP molecule
Identifiers
CAS Number
  • 5502-96-5 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 110475 ☒N
ECHA InfoCard 100.164.946 Edit this at Wikidata
IUPHAR/BPS
  • 2450
PubChem CID
  • 123953
InChI
  • InChI=1S/C21H27N6O18P3/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(44-46(33,34)35)14(29)11(43-20)6-41-48(38,39)45-47(36,37)40-5-10-13(28)15(30)19(42-10)26-3-1-2-9(4-26)21(31)32/h1-4,7-8,10-11,13-16,19-20,28-30H,5-6H2,(H6-,22,23,24,31,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,19-,20-/m1/s1 ☒N
    Key: QOTXBMGJKFVZRD-HISDBWNOSA-O ☒N
SMILES
  • c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)OP(=O)(O)O)O)O)O)C(=O)O
Properties
Chemical formula
[C21H28N6O18P3]+
Molar mass 745.398 g/mol
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

Nicotinic acid adenine dinucleotide phosphate (NAADP) is a Ca2+-mobilizing second messenger synthesised in response to extracellular stimuli. Like its mechanistic cousins, IP3 and cyclic adenosine diphosphoribose (Cyclic ADP-ribose), NAADP binds to and opens Ca2+ channels on intracellular organelles, thereby increasing the intracellular Ca2+ concentration which, in turn, modulates sundry cellular processes (see Calcium signalling). Structurally, it is a dinucleotide that only differs from the house-keeping enzyme cofactor, NADP by a hydroxyl group (replacing the nicotinamide amino group) and yet this minor modification converts it into the most potent Ca2+-mobilizing second messenger yet described. NAADP acts across phyla from plants to humans.

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Nicotinic acid adenine dinucleotide phosphate

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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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Nicotinamide adenine dinucleotide

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Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists...

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Niacin

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component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+). Although niacin and nicotinamide...

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Nicotinamide

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by mouth) to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used for this purpose, niacinamide has the benefit of...

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CD38

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calcium-releasing second messengers cyclic ADP-ribose (cADPR) and nicotinic acid adenine dinucleotide phosphate (NAADP). CD38 is most frequently found on plasma B cells...

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Calcium channel

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Receptor Potential (TRP) channels, Cyclic nucleotide-gated (CNG) channels, Acid-sensing ion channels, and SOC channels. These channels can be regulated by...

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Vitamin B3

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component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+). Although niacin and nicotinamide...

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Calcium signaling

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Recent studies have cited the phospholipase A2 beta, nicotinic acid adenine dinucleotide phosphate (NAADP), and the protein STIM 1 as possible mediators...

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cells. The ectoenzyme has been shown to be important in nicotinic acid adenine dinucleotide phosphate (NAADP) synthesis. NAADP is an intracellular second...

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Nicotinamide mononucleotide

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TFEB

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biogenesis, exocytosis and autophagy. In bacterial infection nicotinic acid adenine dinucleotide phosphate (NAADP) induction of lysosomal Ca2+ efflux and TFEB...

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nicotinamide adenine dinucleotide (NAD+) and produces several neuroactive intermediates including quinolinic acid, kynurenine (KYN), kynurenic acid (KYNA),...

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Antony Galione

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release and globalisation of calcium signals, and that Nicotinic acid adenine dinucleotide phosphate (NAADP) is a ubiquitous trigger for initiating and co-ordinating...

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Dale Sanders

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reticulum of higher plants elicited by the NADP metabolite nicotinic acid adenine dinucleotide phosphate". Proceedings of the National Academy of Sciences. 97...

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Hydroxycarboxylic acid receptor 2

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LSm

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binding-protein for the nucleotide second messenger, NAADP (nicotinic acid adenine dinucleotide phosphate) that activates endo-lysosomal Ca2+ channels TPCs (two-pore...

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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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Kynurenine pathway

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nicotinamide adenine dinucleotide (NAD+). Metabolites involved in the kynurenine pathway include tryptophan, kynurenine, kynurenic acid, xanthurenic acid, quinolinic...

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B vitamins

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nomenclature). Vitamin B13: orotic acid. Vitamin B14: cell proliferant, anti-anemia, rat growth factor, and antitumor pterin phosphate, named by Earl R. Norris...

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Vitamer

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pharmaceutical doses of the nicotinic acid are used under medical supervision as a treatment for hypercholesterolemia. High doses of nicotinic acid are also associated...

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Methylene blue

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mitochondrial respiratory chain, leading to an accumulation of nicotinamide adenine dinucleotide hydrogen (NADH). Methylene blue acts as an alternative electron acceptor...

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Adenosine diphosphate ribose

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cyclic ADP-ribose (cADPR) by the CD38 enzyme using nicotinamide adenine dinucleotide (NAD+) as a cofactor. ADPR binds to and activates the TRPM2 ion channel...

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Dehydroepiandrosterone

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glucose-6-phosphate dehydrogenase (Ki = 17 μM; IC50 = 18.7 μM), and is able to lower NADPHTooltip nicotinamide adenine dinucleotide phosphate levels and...

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Yeast in winemaking

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off-aromas in the resulting wine. Nicotinic acid – involved in the synthesis of Nicotinamide adenine dinucleotide (NAD+), a co-enzyme that is important...

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