N5655

Nicotinic acid adenine dinucleotide phosphate sodium salt

≥92.5%

• Synonym(s): β-NAADP
• Empirical Formula (Hill Notation): C₂₁H₂₇N₆O₁₈P₃ · xNa⁺
• CAS Number: 5502-96-5
• Molecular Weight: 744.39 (free acid basis)
• MDL number: MFCD00274064
• UNSPSC Code: 12352106
• PubChem Substance ID: 24897746
• NACRES: NA.77

Properties

• 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

Description

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⁺.

Safety Information

• 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_germany: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Gloves