Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

N5131

Sigma-Aldrich

Nicotinamide guanine dinucleotide sodium salt

phospodiesterase and ADP-ribosyl cyclase substrate

Synonym(s):

3-(Aminocarbonyl)-1-[(2R,3R,4S,5R)-5-({[(S)-{[(S)-{[(2R,3S,4R,5R)-5-(2-Amino-6-Oxo-1,6-Dihydro-9h-Purin-9-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methoxy}(Hydroxy)phosphoryl]oxy} (Hydroxy)phosphoryl]ox, NGD

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C21H28N7O15P2
CAS Number:
5624-35-1
Molecular Weight:
680.43
MDL number:
MFCD00079505
UNSPSC Code:
41106305
PubChem Substance ID:
24897721
NACRES:
NA.51

form

powder

storage temp.

−20°C

SMILES string

NC(=O)C1=CC=C[N](=C1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5C(=O)N=C(N)Nc45)C(O)C2O

InChI

1S/C21H28N7O15P2/c22-16(33)8-2-1-3-27(4-8)19-14(31)12(29)9(41-19)5-39-44(35,36)43-45(37,38)40-6-10-13(30)15(32)20(42-10)28-7-24-11-17(28)25-21(23)26-18(11)34/h1-4,7,9-10,12-15,19-20,29-32H,5-6H2,(H2,22,33)(H,35,36)(H,37,38)(H3,23,25,26,34)

InChI key

WWXCUPZEUROLRY-UHFFFAOYSA-N

Application

Nicotinamide guanine dinucleotide (NGD+) may be used as a preferred substrate of specific snake Trimeresurus stejnegeri venom phospodiesterase and a substrate to study the specificity and kinetics of ADP-ribosyl cyclase(s).
Nicotinamide guanine dinucleotide sodium salt has been used as a substrate for measuring the cyclase activity of the enzyme cluster of differentiation 38 (CD38). It has also been used as a substrate to fluorometrically determine the activity of CD38/ADP-ribose (ADPR).

Biochem/physiol Actions

Nicotinamide guanine dinucleotide sodium salt is used to determine the activity of proteins that generate cyclic-ADP-ribose (cADPR) in the ADP-ribosyl cyclase family.

Other Notes

Analog of β-NAD

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Large-scale purification of Aplysia ADP-ribosylcyclase and measurement of its activity by fluorimetric assay.
H C Lee et al.
Methods in enzymology, 280, 331-340 (1997-01-01)
C Munshi et al.
Biochimica et biophysica acta, 1388(2), 428-436 (1998-12-22)
ADP-ribosyl cyclase is a multi-functional enzyme that catalyzes the formation of two Ca2+ signaling molecules, cyclic ADP-ribose (cADPR) and nicotinic acid adenine dinucleotide phosphate (NAADP). X-ray crystallography of three different crystal forms shows that it is a non-covalent dimer. Chemical
Measuring CD38 Hydrolase and Cyclase Activities: 1, N6-Ethenonicotinamide Adenine Dinucleotide (varepsilon-NAD) and Nicotinamide Guanine Dinucleotide (NGD) Fluorescence-based Methods
de Oliveira GC, et al.
Bio-protocol, 8(14) (2018)
Lili Peng et al.
Biochimie, 93(9), 1601-1609 (2011-06-15)
The phosphodiesterases (PDEs) are a superfamily of enzymes that have multiple roles in extracellular nucleotide metabolism and in the regulation of nucleotide-based intercellular signaling. Here we describe for the first time the isolation and partial characterization of a novel phosphodiesterase
M E Migaud et al.
Biochemistry, 38(28), 9105-9114 (1999-07-22)
Readily synthesized nicotinamide adenine dinucleotide (NAD(+)) analogues have been used to investigate aspects of the cyclization of NAD(+) to cyclic adenosine 5'-O-diphosphate ribose (cADPR) catalyzed by the enzyme adenosine 5'-O-diphosphate (ADP) ribosyl cyclase and to produce the first potent inhibitors
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service