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C7344

Sigma-Aldrich

Cyclic adenosine diphosphate-ribose

≥90% (HPLC), 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
UNSPSC Code:
41106305
NACRES:
NA.51

biological source

(Ovotestis from sea hare)

Assay

≥90% (HPLC)

form

lyophilized powder

storage temp.

−20°C

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

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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

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

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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)
Yo Sasaki et al.
Experimental neurology, 345, 113842-113842 (2021-08-18)
SARM1 is an inducible NAD+ hydrolase that is the central executioner of pathological axon loss. Recently, we elucidated the molecular mechanism of SARM1 activation, demonstrating that SARM1 is a metabolic sensor regulated by the levels of NAD+ and its precursor
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
Transfer of mitochondria from astrocytes to neurons after stroke
Hayakawa K, et al.
Nature, 535(7613), 551-551 (2016)
Asif Iqbal Shawl et al.
Islets, 1(3), 216-223 (2010-11-26)
Insulin has an autocrine/paracrine role through insulin receptors in pancreatic β-cells. Herein, we show the insulin receptor signaling pathway underlying CD38/ADPR-cyclase activation for NAADP/cADPR formation to induce Ca2+ rise, ultimately resulting in β-cell proliferation. Binding of insulin on insulin receptors
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