CHEBI:64108 - 8-bromo-3',5'-cyclic GMP

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 8-bromo-3',5'-cyclic GMP
ChEBI ID CHEBI:64108
Definition A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1α and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C10H11BrN5O7P
Net Charge 0
Average Mass 424.10100
Monoisotopic Mass 422.95795
InChI InChI=1S/C10H11BrN5O7P/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18)/t2-,4-,5-,8-/m1/s1
InChIKey YUFCOOWNNHGGOD-UMMCILCDSA-N
SMILES Nc1nc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc2c(=O)[nH]1
Roles Classification
Biological Role(s): protein kinase G agonist
An agonist that selectively binds to and activates a protein kinase G receptor.
Application(s): muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 8-bromo-3',5'-cyclic GMP (CHEBI:64108) has functional parent 3',5'-cyclic GMP (CHEBI:16356)
8-bromo-3',5'-cyclic GMP (CHEBI:64108) has role muscle relaxant (CHEBI:51371)
8-bromo-3',5'-cyclic GMP (CHEBI:64108) has role protein kinase G agonist (CHEBI:64105)
8-bromo-3',5'-cyclic GMP (CHEBI:64108) is a 3',5'-cyclic purine nucleotide (CHEBI:19834)
8-bromo-3',5'-cyclic GMP (CHEBI:64108) is a organobromine compound (CHEBI:37141)
IUPAC Name
8-bromoguanosine 3',5'-(hydrogen phosphate)
Synonyms Sources
8-Br-cGMP KEGG COMPOUND
8-Br-Cyclic GMP ChemIDplus
8-Bromo-cgmp ChemIDplus
8-Bromocyclic GMP KEGG COMPOUND
8-Bromocyclic guanosine monophosphate ChemIDplus
8-Bromoguanosine 3',5'-cyclic monophosphate ChemIDplus
8-Bromoguanosine 3',5'-monophosphate ChemIDplus
Manual Xrefs Databases
8-Bromoguanosine_3',5'-cyclic_monophosphate Wikipedia
C13817 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
1233440 Reaxys Registry Number Reaxys
31356-94-2 CAS Registry Number KEGG COMPOUND
31356-94-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10703694 PubMed citation Europe PMC
18509055 PubMed citation Europe PMC
18841072 PubMed citation Europe PMC
21918260 PubMed citation Europe PMC
Last Modified
28 July 2014