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N5655

Nicotinic acid adenine dinucleotide phosphate sodium salt

Name: Nicotinic acid adenine dinucleotide phosphate sodium salt
Brand: SIGMA

≥92.5%, intracellular Ca2+ release activator, solid

Synonym(s):

β-NAADP

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₇N₆O₁₈P₃ · xNa⁺

CAS Number:

5502-96-5

Molecular Weight:

744.39 (free acid basis)

UNSPSC Code:

12352106

PubChem Substance ID:

24897746

NACRES:

NA.77

MDL number:

MFCD00274064

Assay:

≥92.5%

Form:

solid

Quality level:

200

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Product Name

Nicotinic acid adenine dinucleotide phosphate sodium salt, ≥92.5%

Quality Level

200

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Phosphates

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.

Preparation Note

Enzymatically prepared analog of β-NADP⁺.

Other Notes

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

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000521963

0000387977

0000383140

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Nicotinate adenine dinucleotide phosphate (NAADP) triggers a specific calcium release system in sea urchin eggs.

E N Chini et al.

The Journal of biological chemistry, 270(7), 3216-3223 (1995-02-17)

Transient fluxes of intracellular ionized calcium (Ca2+) from intracellular stores are integral components of regulatory signaling pathways operating in numerous biological regulations, including in early stages of egg fertilization. Therefore, we explored whether NADP, which is rapidly generated by phosphorylation

A derivative of NADP mobilizes calcium stores insensitive to inositol trisphosphate and cyclic ADP-ribose.

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).

LRRK2 as a modulator of lysosomal calcium homeostasis with downstream effects on autophagy.

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

Nicotinic acid adenine dinucleotide phosphate (NAADP) is a second messenger in muscarinic receptor-induced contraction of guinea pig trachea.

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)

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Global Trade Item Number

SKU	GTIN
N5655-10MG	04061834117148
N5655-25MG	04061833273180

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