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

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

ChEBI ID	CHEBI:64108
ChEBI Name	8-bromo-3',5'-cyclic GMP
Stars
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.
Last Modified	28 July 2014
Submitter	Steve
Downloads	Molfile

Formula	C10H11BrN5O7P
Net Charge	0
Average Mass	424.104
Monoisotopic Mass	422.95795
SMILES	Nc1nc(=O)c2nc(Br)n([C@@H]3O[C@@H]4COP(=O)(O)O[C@H]4[C@H]3O)c2n1
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

Wikipedia

Roles Classification

Biological Role:

protein kinase G agonist An agonist that selectively binds to and activates a protein kinase G receptor.

Application:

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.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
8-Br-cGMP	KEGG COMPOUND
8-Bromocyclic GMP	KEGG COMPOUND
8-Br-Cyclic GMP	ChemIDplus
8-Bromoguanosine 3',5'-monophosphate	ChemIDplus
8-Bromo-cgmp	ChemIDplus
8-Bromocyclic guanosine monophosphate	ChemIDplus

Manual Xrefs	Databases
C13817	KEGG COMPOUND
8-Bromoguanosine_3',5'-cyclic_monophosphate	Wikipedia

Registry Numbers	Sources
Reaxys:1233440	Reaxys
CAS:31356-94-2	ChemIDplus
CAS:31356-94-2	KEGG COMPOUND

Citations