(6aR,8R,9R,9aS)-8-(6-amino-8-bromo-9H-purin-9-yl)-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,9-dihydroxy-hexahydro-2H-1,3,5,7,2$l^{5},4$l^{5}-furo[3,2-f][1,3,5,2$l^{5},4$l^{5}]trioxadiphosphocine-2,4-dione

• ChemBase ID: 102937
• Molecular Formular: C15H20BrN5O13P2
• Molecular Mass: 620.196522
• Monoisotopic Mass: 618.97162099
• SMILES: [C@H]1(n2c3c(nc2Br)c(ncn3)N)[C@@H]([C@H]2[C@H](O1)COP(=O)(OP(=O)(O2)O[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)OP1(=O)O[C@@H]2[C@@H](COP(=O)(O1)O)O[C@H]([C@@H]2O)n1c(Br)nc2c1ncnc2N
• InChI: InChI=1S/C15H20BrN5O13P2/c16-15-20-6-11(17)18-3-19-12(6)21(15)13-9(25)10-5(30-13)2-29-35(26,27)34-36(28,32-10)33-14-8(24)7(23)4(1-22)31-14/h3-5,7-10,13-14,22-25H,1-2H2,(H,26,27)(H2,17,18,19)/t4-,5-,7-,8-,9-,10-,13-,14+,36?/m1/s1
• InChIKey: PLQQKRPSINJWTK-VNMBDIRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,8R,9R,9aS)-8-(6-amino-8-bromo-9H-purin-9-yl)-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,9-dihydroxy-hexahydro-2H-1,3,5,7,2$l^{5},4$l^{5}-furo[3,2-f][1,3,5,2$l^{5},4$l^{5}]trioxadiphosphocine-2,4-dione; (6aR,8R,9R,9aS)-8-(6-amino-8-bromo-9H-purin-9-yl)-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,9-dihydroxy-hexahydro-2H-1,3,5,7,2λ^5,4λ^5-furo[3,2-f][1,3,5,2λ^5,4λ^5]trioxadiphosphocine-2,4-dione
• IUPAC Traditional name: (6aR,8R,9R,9aS)-8-(6-amino-8-bromopurin-9-yl)-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,9-dihydroxy-tetrahydro-6H-1,3,5,7,2$l^{5},4$l^{5}-furo[3,2-f][1,3,5,2$l^{5},4$l^{5}]trioxadiphosphocine-2,4-dione; (6aR,8R,9R,9aS)-8-(6-amino-8-bromopurin-9-yl)-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,9-dihydroxy-tetrahydro-6H-1,3,5,7,2λ^5,4λ^5-furo[3,2-f][1,3,5,2λ^5,4λ^5]trioxadiphosphocine-2,4-dione
• Synonyms: 8-BR-cADPR; 8-Bromo-cyclic adenosine diphosphate ribose; 8-BROMO-cADP-RIBOSE; Br-cADP-ribose; Br-cADPR; 8-Bromo-cyclic adenosine diphosphate ribose; 8-溴-环二磷酸腺苷核糖

Database IDs

• CAS Number: 151898-26-9
• MDL Number: MFCD00274402
• PubChem SID: 162090315
• PubChem CID: 71299678

CALCULATED PROPERTIES

• Acid pKa: 0.1301163
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -4.468759
• LogD (pH = 7.4): -4.4579387
• Log P: -5.088123
• Molar Refractivity: 114.9691 cm^3
• Polarizability: 47.329746 Å^3
• Polar Surface Area: 260.29 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble5 mg/mL
• Apperance: white lyophilized powder

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 85% (HPLC); 95%
• Empirical Formula (Hill Notation): C15H20BrN5O13P2

DETAILS

MP Biomedicals - 02119133

Ryanodine Receptor
Purity: 95%
This is a cADPR antagonist that blocks the cADPR-induced release of Ca^2+ from sea urchin egg homogenates at 1-3.5uM^45 .

Sigma Aldrich - B5416

Biochem/physiol Actions
An antagonist of cyclic ADP-ribose (cADPR), and an endogenous metabolite of β-NAD+. cADPR has been shown to regulate calcium release from the endoplasmic and sarcoplasmic reticulum. In cells, cADPR is synthesized by ADP-ribosyl cyclase or CD38, a lymphocyte differentiation antigen.
Preparation Note
Prepared enzymatically
Physical form
Lyophilized powder containing 10-20% sodium phosphate buffer salts