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

• ChemBase ID: 105609
• Molecular Formular: C10H11BrN5O6P
• Molecular Mass: 408.102001
• Monoisotopic Mass: 406.96303173
• SMILES: Brc1nc2c(ncnc2n1[C@@H]1O[C@@H]2COP(=O)(O[C@H]2[C@H]1O)O)N
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1c(Br)nc2c1ncnc2N
• InChI: InChI=1S/C10H11BrN5O6P/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)/t3-,5-,6-,9-/m1/s1
• InChIKey: DVKQVRZMKBDMDH-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-(6-amino-8-bromo-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• IUPAC Traditional name: 8-Br-cAMP
• Synonyms: 8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP; 8-Bromoadenosine 3',5'-cyclic monophosphate; 8-Bromoadenosine 3′,5′-cyclic monophosphate; 8-BROMOADENOSINE-3',5'-cyclic-MONOPHOSPHATE; 8-溴腺苷3′,5′-环单磷酸

Database IDs

• CAS Number: 23583-48-4
• EC Number: 245-760-6
• MDL Number: MFCD00075580
• Beilstein Number: 591930
• PubChem SID: 162092597; 24891835
• PubChem CID: 32014
• CHEMBL: 85519
• Chemspider ID: 29689
• Wikipedia Title: 8-Bromoadenosine_3',5'-cyclic_monophosphate

CALCULATED PROPERTIES

• Acid pKa: 1.8298044
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.6202507
• LogD (pH = 7.4): -2.6301942
• Log P: -2.3923864
• Molar Refractivity: 77.9143 cm^3
• Polarizability: 31.093891 Å^3
• Polar Surface Area: 154.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble50 mg/mL, clear, faintly yellow or pink; aqueous base: soluble
• Melting Point: 254 °C (dec.)(lit.)

Safety Information

• Storage Condition: 0°C, Desiccate, Protect from light
• 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: >95%; ≥98.0% (HPLC); 98%
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C10H11BrN5O6P

DETAILS

MP Biomedicals - 02193460

Purity: >95%
cAMP analog more resistant to phosphodiesterases than cAMP. Activates cAMP-dependent protein kinase.

Sigma Aldrich - B5386

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Caution
对光和水分敏感。
Other Notes
膜渗透性 cAMP 类似物。
Biochem/physiol Actions
比 cAMP 更抗磷酸二酯酶水解的细胞通透性 cAMP 类似物。激活培养细胞的蛋白激酶 A、抑制生长、减少增殖、增加分化并诱导凋亡。

Sigma Aldrich - 372447

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 - 16137

Other Notes
Membrane-permeable cAMP analog.
Cyclic nucleotide analog for studying Ca2+- mediated pathways1,2; Potent activator of protein kinase3
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.