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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

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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

biological source

yeast

Quality Level

200

Assay

≥-96%

form

powder

solubility

H2O: soluble-50 mg/mL, clear, almost colorless to slightly yellow

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

N5131-5MG:
N5131-BULK:
N5131-25MG:
N5131-VAR:
N5131-2MG:

Certificates of Analysis (COA)

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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
Leanne T Breen et al.
American journal of physiology. Renal physiology, 290(2), F486-F495 (2005-09-29)
Endogenous nucleotides with extracellular functions may be involved in the complex neural control of human urinary bladder (HUB). Using HPLC techniques with fluorescence detection, we observed that in addition to ATP and its metabolites ADP, AMP and adenosine, electrical field
ADP-ribosyl cyclase and GDP-ribosyl cyclase activities are not always equivalent: impact on the study of the physiological role of cyclic ADP-ribose.
Frances E Lund et al.
Analytical biochemistry, 346(2), 336-338 (2005-10-11)
Decreased ADP-ribosyl cyclase activity in peripheral blood mononuclear cells from diabetic patients with nephropathy.
Ohtsuji M, Yagi K, Shintaku-Kubota M, et al.
EXS, 2008, 508-508 (2008)
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
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