8-Bromoguanosine 3',5'-cyclic monophosphate

8-Bromoguanosine 3',5'-cyclic monophosphate

Names
IUPAC name 2-amino-8-bromo-9-[(1S,6R,8R,9R)-3,9-dihydroxy-3-oxo-2,4,7-trioxa-3λ^5-phosphabicyclo[4.3.0]nonan-8-yl]-3H-purin-6-one
Other names 8-Bromocyclic GMP;8-Bromo-cGMP; 8-Br-cyclic GMP; 8-Br-cGMP
Identifiers
CAS Number	31356-94-2
ChEBI	CHEBI:64108
ChemSpider	94575
Jmol interactive 3D	Image Image
PubChem	104767
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 Key: YUFCOOWNNHGGOD-UMMCILCDSA-N InChI=1/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 Key: YUFCOOWNNHGGOD-UMMCILCDBZ
SMILES C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=C(C(=O)N=C(N4)N)N=C3Br)O)OP(=O)(O1)O O=C4/N=C(/N)Nc1c4nc(Br)n1[C@@H]2O[C@@H]3COP(=O)(O[C@H]3[C@H]2O)O
Properties
Chemical formula	C10H11BrN5O7P
Molar mass	424.10 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

8-Bromoguanosine 3',5'-cyclic monophosphate is a brominated derivative of cyclic guanosine monophosphate (cGMP).^[1] It acts as an activator of cGMP-dependent protein kinases.^[2]

See also

• 8-Bromoadenosine 3',5'-cyclic monophosphate (8-Br-cAMP)

References

1. Rapoport, RM; Draznin, MB; Murad, F (Nov 1982). "Sodium nitroprusside-induced protein phosphorylation in intact rat aorta is mimicked by 8-bromo cyclic GMP" (Free full text). Proceedings of the National Academy of Sciences of the United States of America 79 (21): 6470–4. doi:10.1073/pnas.79.21.6470. ISSN 0027-8424. PMC 347148. PMID 6292902.
2. 8-Bromoguanosine-3',5'-cyclic monophosphate ( 8-Br-cGMP )