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8-bromo-3',5'-cyclic GMP

Go to external page http://purl.obolibrary.org/obo/CHEBI_64108

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 PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.

Term info

Label

8-bromo-3',5'-cyclic GMP

Synonyms
  • 8-bromoguanosine 3',5'-(hydrogen phosphate)
database cross reference
Subsets

3_STAR

IUPAC NAME
8-bromoguanosine 3',5'-(hydrogen phosphate) [ IUPAC ]

charge

0

formula

C10H11BrN5O7P

has obo namespace

chebi_ontology

has related synonym

8-Br-Cyclic GMP, 8-Bromoguanosine 3',5'-cyclic monophosphate, 8-Br-cGMP, 8-Bromocyclic guanosine monophosphate, 8-Bromo-cgmp, 8-Bromocyclic GMP, 8-Bromoguanosine 3',5'-monophosphate

id

CHEBI:64108

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

mass

424.10100

monoisotopicmass

422.95795

smiles

Nc1nc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc2c(=O)[nH]1