8-Bromoadenosine 3',5'-cyclic monophosphate

8-Bromoadenosine 3',5'-cyclic adenosine 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]

8-Bromoadenosine 3',5'-cyclic monophosphate[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
8-Bromoadenosine 3′,5′-(hydrogen phosphate)
Systematic IUPAC name
(4aR,6R,7R,7aS)-6-(6-Amino-8-bromo-9H-purin-9-yl)-2,7-dihydroxytetrahydro-2H,4H-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
Other names
8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.041.585
UNII
  • 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 ☒N
    Key: DVKQVRZMKBDMDH-UUOKFMHZSA-N ☒N
  • Brc2nc1c(ncnc1n2[C@@H]3O[C@@H]4COP(=O)(O[C@H]4[C@H]3O)O)N
Properties
C10H11BrN5O6P
Molar mass 408.105 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

See also

References
  1. 8-Bromoadenosine 3′,5′-cyclic monophosphate at Sigma-Aldrich
  2. 8-Bromo Cyclic Adenosine Monophosphate at PubChem
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