8-Bromoadenosine 3',5'-cyclic monophosphate

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8-Bromoadenosine 3',5'-cyclic monophosphate^[1]


IUPAC name (1S,6R,8R,9R)-8-(6-amino-8-bromopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3λ⁵-phosphabicyclo[4.3.0]nonan-9-ol
Other names 8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP
Identifiers
CAS number	23583-48-4
PubChem	32014
ChemSpider	1839^Y
ChEMBL	CHEMBL85519^Y
Jmol-3D images	Image 1
SMILES Brc2nc1c(ncnc1n2C4OC3COP(=O)(OC3C4O)O)N
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)^Y Key: DVKQVRZMKBDMDH-UHFFFAOYSA-N^Y InChI=1/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) Key: DVKQVRZMKBDMDH-UHFFFAOYAI
Properties
Molecular formula	C₁₀H₁₁BrN₅O₆P
Molar mass	408.1 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

8-Bromoadenosine 3',5'-cyclic monophosphate (8-Br-cAMP) is a brominated derivative of cyclic adenosine monophosphate (cAMP). 8-Br-cAMP is an activator of cyclic AMP-dependent protein kinase, and it is long-acting because it is resistant to degradation by cyclic AMP phosphodiesterase.^[2]

References

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