8-Bromoadenosine 3',5'-cyclic monophosphate

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

Names
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
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL85519 Y
ChemSpider	29689
ECHA InfoCard	100.041.585
PubChem	32014
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 Key: DVKQVRZMKBDMDH-UUOKFMHZSA-N 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)/t3-,5-,6-,9-/m1/s1 Key: DVKQVRZMKBDMDH-UUOKFMHZBM
SMILES Brc2nc1c(ncnc1n2[C@@H]3O[C@@H]4COP(=O)(O[C@H]4[C@H]3O)O)N
Properties
Chemical formula	C10H11BrN5O6P
Molar mass	408.10 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

See also

• 8-Bromoguanosine 3',5'-cyclic monophosphate (8-Br-cGMP)

References