sodium (4aR,6R,7R,7aS)-6-(6-amino-8-bromo-9H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 105121
• Molecular Formular: C10H10BrN5NaO6P
• Molecular Mass: 430.083831
• Monoisotopic Mass: 428.94497598
• SMILES: [Na+].Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@@H]2COP(=O)([O-])O[C@H]2[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Br)nc2c1ncnc2N.[Na+]
• InChI: InChI=1S/C10H11BrN5O6P.Na/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6;/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1
• InChIKey: DMRMZQATXPQOTP-GWTDSMLYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-(6-amino-8-bromo-9H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• IUPAC Traditional name: sodium (4aR,6R,7R,7aS)-6-(6-amino-8-bromopurin-9-yl)-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: 8-Br-cAMP; 8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt; 8-BROMOADENOSINE-3',5'-cyclic-MONOPHOSPHATE SODIUM SALT

Database IDs

• CAS Number: 76939-46-3
• MDL Number: MFCD00005844
• Beilstein Number: 7739743
• PubChem SID: 162091861; 24278020
• PubChem CID: 23702958

CALCULATED PROPERTIES

• Acid pKa: 1.8298044
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.6202507
• LogD (pH = 7.4): -2.6301942
• Log P: -2.3923864
• Molar Refractivity: 76.7926 cm^3
• Polarizability: 30.974596 Å^3
• Polar Surface Area: 157.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL
• Apperance: off-white powder

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC); ≥98.0% (HPLC); 98%
• Impurities: ≤2% adenosine-3′,5′-cyclophosphate (HPLC)
• Empirical Formula (Hill Notation): C10H10BrN5NaO6P

DETAILS

MP Biomedicals - 02158877

Sodium Salt
Purity: 98%
cAMP analog more resistant to phosphodiesterases than cAMP. Activates cAMP-dependent protein kinase.

Sigma Aldrich - B7880

Caution
Sensitive to light and moisture.
Other Notes
Membrane-permeable cAMP analog.
Biochem/physiol Actions
Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. Activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.

Sigma Aldrich - 16135

Other Notes
Membrane-permeable cAMP analog.
Inhibits the transient expression of firefly luciferase1
Biochem/physiol Actions
Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. Activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.

REFERENCES

• Meyer, R.B. and Miller, J.P., Life Sci. , 14 : 1019, (1974)
• Hei, Y.-J., et.al., Mol. Pharmacol. , 39 : 223, (1991)
• Sandberg, M., et.al., Biochem. J. , 279 : 521, (1991).