CHEBI:64211 - 8-Br-cAMP

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ChEBI Name 8-Br-cAMP
ChEBI ID CHEBI:64211
Definition A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Kalpana P
Secondary ChEBI IDs CHEBI:84608, CHEBI:145729
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Formula C10H11BrN5O6P
Net Charge 0
Average Mass 408.10200
Monoisotopic Mass 406.96303
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
SMILES Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12
Roles Classification
Biological Role(s): protein kinase agonist
An agonist that selectively binds to and activates a protein kinase receptor.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 8-Br-cAMP (CHEBI:64211) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-Br-cAMP (CHEBI:64211) has role antidepressant (CHEBI:35469)
8-Br-cAMP (CHEBI:64211) has role protein kinase agonist (CHEBI:64106)
8-Br-cAMP (CHEBI:64211) is a 3',5'-cyclic purine nucleotide (CHEBI:19834)
8-Br-cAMP (CHEBI:64211) is a adenyl ribonucleotide (CHEBI:61296)
8-Br-cAMP (CHEBI:64211) is a organobromine compound (CHEBI:37141)
IUPAC Name
8-bromoadenosine 3',5'-(hydrogen phosphate)
Synonyms Sources
(4aR,6R,7R,7aS)-6-(6-amino-8-bromo-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide IUPAC
8-bromo cyclic adenosine monophosphate ChemIDplus
8-bromo-cAMP ChEBI
8-Bromo-cAMP ChEBI
8-bromo-cyclic 3',5'-AMP ChemIDplus
8-bromo-cyclic AMP ChemIDplus
8-bromoadenosine 3',5'-cyclic monophosphate ChemIDplus
8-bromoadenosine 3',5'-monophosphate ChemIDplus
8-bromoadenosine cyclic 3',5'-phosphate ChemIDplus
BCAMP ChemIDplus
cyclic 8-bromoadenosine 3',5'-monophosphate ChemIDplus
Manual Xref Database
8-Bromoadenosine_3',5'-cyclic_monophosphate Wikipedia
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Registry Numbers Types Sources
23583-48-4 CAS Registry Number ChemIDplus
591930 Reaxys Registry Number Reaxys
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Last Modified
02 January 2020