cyclic ADP-ribose

Base Information

• Chemical Name: cyclic ADP-ribose
• CAS No.: 119340-53-3
• Deprecated CAS: 143822-66-6,150155-83-2,1018828-36-8
• Molecular Formula: C15H21 N5 O13 P2
• Molecular Weight: 541.305
• European Community (EC) Number: 634-254-4
• UNII: Q780BR06V8
• DSSTox Substance ID: DTXSID50896995
• Nikkaji Number: J626.674F
• Wikipedia: Cyclic_ADP-ribose
• Wikidata: Q2467043,Q27459000
• Pharos Ligand ID: T6JH394W5TF5
• Metabolomics Workbench ID: 54399
• Mol file: 119340-53-3.mol

Synonyms:Adenosine Diphosphate Ribose, Cyclic;ADP-Ribose, Cyclic;ADPribose, Cyclic;cADP Ribose;cADP-Ribose;cADPR;Cyclic Adenosine Diphosphate Ribose;Cyclic ADP Ribose;Cyclic ADP-Ribose;Cyclic ADPribose

Chemical Property of cyclic ADP-ribose

Chemical Property:

• Appearance/Colour: Lyophilized powder
• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 934.8 °C at 760 mmHg
• PKA: 0.97±0.70(Predicted)
• Flash Point: 519.1 °C
• PSA: 276.92000
• Density: 2.57 g/cm³
• LogP: -2.29370
• Storage Temp.: -20°C
• XLogP3: -5.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 0
• Exact Mass: 541.06110974
• Heavy Atom Count: 35
• Complexity: 989

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclic adenosine diphosphate-ribose ≥90% (HPLC), lyophilized powder ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=CN(C4=N)C5C(C(C(O5)COP(=O)(OP(=O)(O1)O)O)O)O)O)O
• Isomeric 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
• Uses: 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.

Technology Process of cyclic ADP-ribose

There total 5 articles about cyclic ADP-ribose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

NAD (53-84-9,66844-06-2) → adenosine 5′-diphosphate ribose (47774-99-2,47775-00-8,88495-30-1) + nicotinamide (98-92-0,1255150-40-3) + cyclic adenosine 5'-diphosphate ribose (119340-53-3)

Guidance literature:

With triethylamine; sodium bromide; In dimethyl sulfoxide; at 70 ℃; for 2h; Mechanism; Product distribution; other metal halides, var. reaction time;

Reference yield:

NAD (53-84-9,66844-06-2) → cyclic adenosine 5'-diphosphate ribose (119340-53-3)

Guidance literature:

With sodium phosphate buffer; at 37 ℃; for 0.5h; pig brain acetone powder;

DOI:10.1021/ja00096a002

Reference yield:

phosphoribosyl ATP (1110-99-2,157496-83-8) → cyclic adenosine 5'-diphosphate ribose (119340-53-3) + Phosphoric acid mono-{(2R,3S,4R,5R)-5-[1-((2R,3R,4S,5R)-3,4-dihydroxy-5-phosphonooxymethyl-tetrahydro-furan-2-yl)-6-imino-1,6-dihydro-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl} ester

Guidance literature:

With HEPES buffer; magnesium chloride; In acetonitrile; at 24 ℃; for 48h; pig liver NAD⁺ pyrophosphorylase, yeast inorganic pyrophosphatase;

DOI:10.1021/ja00096a002

upstream raw materials:

NAD

phosphoribosyl ATP

alpha-NAD

nicotinamide adenine dinucleotide

Refernces

• 1、 Gu, Qu-Ming,Sih, Charles J.. "Cyclic ADP-ribose: Synthesis and structural assignment". . p. 7481 - 7486. Retrieved 1994.
• 2、 Yamada, Shinji,Gu, Qu-Ming,Sih, Charles J.. "Cyclic ADP-ribose via stereoselective cyclization of β-NAD". . p. 10787 - 10788. Retrieved 2007/10/02.