Cyclic ADP-ribose

Names

[ CAS No. ]:
119340-53-3

[ Name ]:
Cyclic ADP-ribose

[Synonym ]:
cyclic ADP-D-ribose
Enzyme-activated NAD
adenosine 5'-cyclic-diphosphoribose
cyclic adenosine 5'-diphosphoribose
cADP-Ribose
Cyclic Adenosine Diphosphate Ribose
E-NAD
cADPR
Cyclic ADPR
cyclic adenosine 5'-diphosphate ribose
MFCD00214262

Biological Activity

[Description]:

Cyclic ADP-ribose (cADPR) is a potent second messenger for calcium mobilization that is synthesized from NAD+ by a ADP-ribosyl cyclase. Cyclic ADP-ribose increases cytosolic calcium mainly by Ryanodine receptor-mediated release from endoplasmic reticulum and also by extracellular influx through the opening of TRPM2 channels[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Cardiovascular Disease

Research Areas >> Endocrinology

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[Target]

Calcium mobilization[1] TRPM2 channels[1] Endogenous metabolite[1]

[In Vitro]

In cells, Cyclic ADP-ribose (cADPR) is an important player in processes such as: cell proliferation and differentiation, regulating e.g. expansion of human mesenchymal stem cells and hemopoietic progenitors, neuronal differentiation of PC12 cells, and cardiomyocyte differentiation of mouse embryonic stem cells[1].

[In Vivo]

In mammals, Cyclic ADP-ribose (cADPR) is an important player in processes such as: inflammatory and immune responses, including neutrophil chemotaxis and T cell activation; smooth muscle cell contraction in arteries and bronchi, with participation in the hypoxic pulmonary vasoconstriction and in the pathogenesis of inflammatory/allergic airway diseases; myometrium contractility, eventually contributing to delivery; myocyte contraction in adult cardiac tissue, participating in angiotensin II- and β-adrenergic-induced cardiac hypertrophy and in isoproterenol-induced arrhythmias; endocrine and exocrine pancreatic secretion; and social behaviour in mice, including memory formation and spatial learning, related to oxytocin secretion and maybe to niacin deficiency[1]. Furthermore, Cyclic ADP-ribose (cADPR) is involved in egg activation and fertilization in ascidians and sea urchin, in early development in sea urchin, in abscisic acid signalling in sponges and plants, in cell fission in dinoflagellates, and in Toxoplasma gondii pathogenicity[1].

[References]

[1]. Ribeiro JM, et al. Specific cyclic ADP-ribose phosphohydrolase obtained by mutagenic engineering of Mn2+-dependent ADP-ribose/CDP-alcohol diphosphatase. Sci Rep. 2018 Jan 18;8(1):1036.

Chemical & Physical Properties

[ Density]:
2.57 g/cm3

[ Boiling Point ]:
934.8ºC at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₁N₅O₁₃P₂

[ Molecular Weight ]:
541.30000

[ Flash Point ]:
519.1ºC

[ Exact Mass ]:
541.06100

[ PSA ]:
276.92000

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.959

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Cyclic ADP-ribose requires CD38 to regulate the release of ATP in visceral smooth muscle.

FEBS J. 278 , 3095-3108, (2011)

It is well established that the intracellular second messenger cADP-ribose (cADPR) activates Ca(2+) release from the sarcoplasmic reticulum through ryanodine receptors. CD38 is a multifunctional enzym...

β-Adrenergic receptor signaling increases NAADP and cADPR levels in the heart.

Biochem. Biophys. Res. Commun. 427(2) , 326-9, (2012)

Evidence suggests that β-Adrenergic receptor signaling increases heart rate and force through not just cyclic AMP but also the Ca(2+)-releasing second messengers NAADP (nicotinic acid adenine dinucleo...

Pyridine nucleotide metabolites and calcium release from intracellular stores.

Adv. Exp. Med. Biol. 740 , 305-23, (2012)

Ca(2+) signals are probably the most common intracellular signaling elements, controlling an extensive range of responses in virtually all cells. Many cellular stimuli, often acting at cell surface re...

Cyclic ADP-​ribose