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Merck

N5655

Sigma-Aldrich

Nicotinic acid adenine dinucleotide phosphate sodium salt

≥92.5%

Sinónimos:

β-NAADP

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About This Item

Fórmula empírica (notación de Hill):
C21H27N6O18P3 · xNa+
Número de CAS:
Peso molecular:
744.39 (free acid basis)
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

assay

≥92.5%

form

solid

storage temp.

−20°C

SMILES string

[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)OCC4O[C@@H]([C@@H](O)[C@H]4O)[n+]5cccc(c5)C(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O

InChI

1S/C21H27N6O18P3.Na/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);/q;+1/p-1/t10?,11-,13+,14-,15+,16-,19+,20-;/m1./s1

InChI key

KKCRODBDXQTAPI-NZNNTXIPSA-M

Categorías relacionadas

General description

NAADP induces Ca2+ release from the eggs of sea urchin, when injected into the cell. It can be enzymatically produced from nicotinamide adenine dinucleotide phosphate (β-NADP) with the help of ADP-ribosyl cyclase.

Application

Nicotinic acid adenine dinucleotide phosphate sodium salt has been used for agonist injection into unfertilized eggs and embryos.

Biochem/physiol Actions

Potent activator of intracellular Ca2+ release via an IP3 and cyclic ADP ribose-independent mechanism.

Other Notes

Note: Should not be confused with nicotinamide adenine dinucleotide phosphate (NADP).

Preparation Note

Enzymatically prepared analog of β-NADP+.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Parvinder K Aley et al.
The Journal of biological chemistry, 288(16), 10986-10993 (2013-03-08)
Nicotinic acid adenine dinucleotide phosphate (NAADP) is increasingly being demonstrated to be involved in calcium signaling in many cell types and species. Although it has been shown to play a role in smooth muscle cell contraction in several tissues, nothing
Slow calcium waves mediate furrow microtubule reorganization and germ plasm compaction in the early zebrafish embryo
Eno C, et al.
Development (2018)
H C Lee et al.
The Journal of biological chemistry, 270(5), 2152-2157 (1995-02-03)
We have previously shown that alkaline treatment of NADP generates a derivative which can mobilize Ca2+ from sea urchin egg homogenates (Clapper, D. L., Walseth, T. F., Dargie, P. J., and Lee, H. C. (1987) J. Biol. Chem. 262, 9561-9568).
Patricia Gómez-Suaga et al.
Autophagy, 8(4), 692-693 (2012-03-24)
Alterations in autophagy are thought to underlie various neurodegenerative diseases including Parkinson disease (PD). Previous studies have indicated that the PD gene leucine rich repeat kinase 2 (LRRK2) is involved in this process, but its mechanism of action has remained
Lianne C Davis et al.
Current biology : CB, 22(24), 2331-2337 (2012-11-28)
A cytotoxic T lymphocyte (CTL) kills an infected or tumorigenic cell by Ca(2+)-dependent exocytosis of cytolytic granules at the immunological synapse formed between the two cells. Although inositol 1,4,5-trisphosphate (IP(3))-mediated Ca(2+) release from the endoplasmic reticulum activates the store-operated Ca(2+)-influx

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