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Merck

C7344

Cyclic adenosine diphosphate-ribose

≥90% (HPLC), from Ovotestis from sea hare, lyophilized powder

Synonym(s):

ADP-cyclo[N1:1′′]-ribose, Cyclic ADPR, cADP-ribose, cADPR

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About This Item

Empirical Formula (Hill Notation):
C15H21N5O13P2
CAS Number:
119340-53-3
Molecular Weight:
541.30
MDL number:
MFCD00214262
UNSPSC Code:
41106305
NACRES:
NA.51
Assay:
≥90% (HPLC)
Biological source:
(Ovotestis from sea hare)
Form:
lyophilized powder
Solubility:
water: 5 mg/mL, clear, colorless
Storage temp.:
−20°C

Key Documents

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Product Name

Cyclic adenosine diphosphate-ribose, ≥90% (HPLC), lyophilized powder

SMILES string

O[C@H]1[C@@H](O)[C@H]2O[C@@H]1COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)[n@H]4cnc5C(=N)[N@@H]2C=Nc45

InChI

1S/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1

InChI key

BQOHYSXSASDCEA-KEOHHSTQSA-N

biological source

(Ovotestis from sea hare)

assay

≥90% (HPLC)

form

lyophilized powder

solubility

water: 5 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Cyclic adenosine diphosphate-ribose (cADPR) is an intracellular second messenger that mobilizes intracellular Ca2+ release from the sarcoplasmic reticulum through ryanodine receptors. CADPR is also a second messenger for glucose-induced insulin release from endocrine pancreas and for abscisic acid-induced calcium release in plants.
Cyclic adenosine diphosphate-ribose has been used to stimulate astrocytes to activate CD38 signaling. It has also been used as a supplement in buffered peptone water to recover S. enteritidis.

Biochem/physiol Actions

Mobilizes intracellular Ca2+; regulates Ca2+-induced Ca2+ release specifically blocked by ryanodine; second messenger for glucose-induced insulin release from the endocrine pancreas and for abscisic acid-induced calcium release in plants.

Packaging

Package size based on nucleotide content.

Physical form

Lyophilized powder

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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.

C7344-250UG: + C7344-.5MG: + C7344-VAR: + C7344-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SLCF8370
SLCC5961
SLBW5417
SLBN2062V
047K5059

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Shunichi Kajioka et al.
The Journal of urology, 186(2), 736-744 (2011-06-21)
To clarify the properties of adenosine triphosphate sensitive K+ channel in human detrusor smooth muscle we examined the effect of the representative nicotinic acid derivatives β-nicotinamide adenine dinucleotide, cyclic adenosine diphosphate ribose and nicotinic acid adenine dinucleotide phosphate (Sigma-Aldrich®) on
Effects of carob bean gum on performance, nutrient digestibility and Salmonella enterica var. Enteritidis colonisation in chickens
Vila B, et al.
Food Research International, 45(2), 1133-1138 (2012)
Hon Cheung Lee
Science China. Life sciences, 54(8), 699-711 (2011-07-26)
The concept advanced by Berridge and colleagues that intracellular Ca(2+)-stores can be mobilized in an agonist-dependent and messenger (IP(3))-mediated manner has put Ca(2+)-mobilization at the center stage of signal transduction mechanisms. During the late 1980s, we showed that Ca(2+)-stores can
Yong Juan Zhao et al.
Science signaling, 5(241), ra67-ra67 (2012-09-13)
The transmembrane enzyme CD38, a multifunctional protein ubiquitously present in cells, is the main enzyme that synthesizes and hydrolyzes cyclic adenosine 5'-diphosphate-ribose (cADPR), an intracellular Ca(2+)-mobilizing messenger. CD38 is thought to be a type II transmembrane protein with its carboxyl-terminal
H C Lee et al.
The Journal of biological chemistry, 264(3), 1608-1615 (1989-01-25)
Incubation of NAD+ with extracts from sea urchin eggs resulted in production of a metabolite which could mobilize intracellular Ca2+ stores of the eggs. In this study we present structural evidence indicating that the metabolite is a cyclized ADP-ribose having
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