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N5655 Sigma-Aldrich

Nicotinic acid adenine dinucleotide phosphate sodium salt

≥92.5%

Synonym: β-NAADP

  • CAS Number 5502-96-5

  • Empirical Formula (Hill Notation) C21H27N6O18P3 · xNa+

  • Molecular Weight 744.39 (free acid basis)

  •  MDL number MFCD00274064

  •  PubChem Substance ID 24897746

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
assay   ≥92.5%
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.

Packaging

10, 25 mg in poly bottle

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).

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N5655.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Preparation Note

Enzymatically prepared analog of β-NADP+.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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