Physicochemical Properties
| Molecular Formula | C15H21N5O13P2 |
| Molecular Weight | 541.30054 |
| Exact Mass | 541.061 |
| CAS # | 119340-53-3 |
| Related CAS # | Cyclic ADP-ribose ammonium |
| PubChem CID | 123847 |
| Appearance | White to off-white solid powder |
| Density | 2.57 g/cm3 |
| Boiling Point | 934.8ºC at 760 mmHg |
| Flash Point | 519.1ºC |
| Vapour Pressure | 0mmHg at 25°C |
| Index of Refraction | 1.959 |
| LogP | -5.7 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 35 |
| Complexity | 989 |
| Defined Atom Stereocenter Count | 8 |
| SMILES | C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CN(C4=N)[C@H]5[C@@H]([C@@H]([C@H](O5)COP(=O)(OP(=O)(O1)O)O)O)O)O)O |
| InChi Key | BQOHYSXSASDCEA-KEOHHSTQSA-N |
| InChi Code | 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 |
| Chemical Name | (2R,3R,4S,5R,13R,14S,15R,16R)-8,10-dihydroxy-24-imino-8,10-dioxo-7,9,11,25,26-pentaoxa-1,17,19,22-tetraza-8λ5,10λ5-diphosphapentacyclo[18.3.1.12,5.113,16.017,21]hexacosa-18,20,22-triene-3,4,14,15-tetrol |
| Synonyms | Cyclic ADPribose; Cyclic ADP ribose |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In homogenates of sea urchin eggs, cADPR (20 nM) causes a large and quick release of Ca2+ [1]. In a subgroup of cultured astrocytes (64%) cADPR (100 µM; 10 min) generates a sustained rise in intracellular calcium concentration [4]. Oxytocin (OT) is released from the isolated hypothalamus of cultured male mice in response to cADPR (100 µM) and heat (35–38.5°C) [5]. |
| ln Vivo | In longitudinal or slave mice, cADPR (100 µM; push-pull cerebral microperfusion) raises OT concentrations [5]. |
| References |
[1]. Ca(2+)-induced Ca2+ release in sea urchin egg homogenates: modulation by cyclic ADP-ribose. Science. 1991 Sep 6;253(5024):1143-6. [2]. Structural determination of a cyclic metabolite of NAD+ with intracellular Ca2+-mobilizing activity. J Biol Chem. 1989 Jan 25;264(3):1608-15. [3]. 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. [4]. Evidence of a role for cyclic ADP-ribose in calcium signalling and neurotransmitter release in cultured astrocytes. J Neurochem. 2001 Aug;78(3):646-57. [5]. Cyclic ADP-Ribose and Heat Regulate Oxytocin Release via CD38 and TRPM2 in the Hypothalamus during Social or Psychological Stress in Mice. Front Neurosci. 2016 Jul 22;10:304. |
| Additional Infomation |
Cyclic ADP-beta-D-ribose is a cyclic purine nucleotide that is synthesised from NAD+ by ADP-ribosyl cyclase; acts as an agonist at ryanodine receptors. It has a role as a ryanodine receptor agonist and a metabolite. It is a cyclic purine nucleotide and a nucleotide-sugar. It is functionally related to an ADP-beta-D-ribose. It is a conjugate acid of a cyclic ADP-beta-D-ribose(2-). cyclic ADP-ribose has been reported in Psychotria punctata, Ardisia crenata, and Apis cerana with data available. A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE. |
Solubility Data
| Solubility (In Vitro) | H2O : ~5 mg/mL (~9.24 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8474 mL | 9.2370 mL | 18.4740 mL | |
| 5 mM | 0.3695 mL | 1.8474 mL | 3.6948 mL | |
| 10 mM | 0.1847 mL | 0.9237 mL | 1.8474 mL |