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8-Bromoadenosine 3',5'-cyclic monophosphate

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8-Bromoadenosine 3',5'-cyclic monophosphate
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-2λ-furodioxaphosphinin-2-one
Other names 8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.041.585 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: DVKQVRZMKBDMDH-UUOKFMHZSA-N
SMILES
  • Brc2nc1c(ncnc1n23O4COP(=O)(O43O)O)N
Properties
Chemical formula C10H11BrN5O6P
Molar mass 408.105 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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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