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N5131

Nicotinamide guanine dinucleotide sodium salt

Name: Nicotinamide guanine dinucleotide sodium salt
Brand: SIGMA

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

NACRES:

NA.51

PubChem Substance ID:

24897721

UNSPSC Code:

41106305

MDL number:

MFCD00079505

Form:

powder

Assay:

≥-96%

Solubility:

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

Biological source:

yeast

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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 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).

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).

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

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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Synthesis of NAADP and cADPR in mitochondria.

M Liang et al.

Archives of biochemistry and biophysics, 371(2), 317-325 (1999-11-05)

Here we investigated whether cADPR and NAADP are synthesized in mitochondria. We found that ADPR-cyclase activity is present in mitochondria. In addition, we describe for the first time synthesis of NAADP in this intracellular organelle. ADPR-cyclase activities (V(MAX)) and NAADP

Probing Aplysia californica adenosine 5'-diphosphate ribosyl cyclase for substrate binding requirements: design of potent inhibitors.

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

Sarcoplasmic reticulum-associated and protein kinase C-regulated ADP-ribosyl cyclase in cardiac muscle.

L G Mészáros et al.

Biochemical and biophysical research communications, 234(1), 252-256 (1997-05-08)

Two types of ADP-ribosyl cyclase activity were distinguished in dog and rat cardiac muscles by measuring the enzymatic conversion of NGD (as an NAD analog) into the fluorescent product cyclic GDP-ribose in cardiac muscle subcellular fractions. Both types of activity

Catalytic properties of the retinal rod outer segment disk ADP-ribosyl cyclase.

Andrea Fabiano et al.

Visual neuroscience, 28(2), 121-128 (2011-01-29)

Cyclic ADP-ribose (cADPR) is a second messenger modulating intracellular calcium levels. We have previously described a cADPR-dependent calcium signaling pathway in bovine rod outer segments (ROS), where calcium ions play a pivotal role. ROS ADP-ribosyl cyclase (ADPR-cyclase) was localized in

The homo-dimeric form of ADP-ribosyl cyclase in solution.

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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Global Trade Item Number

SKU	GTIN
N5131-5MG	04061833264256
N5131-25MG	04061833631089

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