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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:8-bromo-3',5'-cyclic GMP
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Accession:CHEBI:64108 term browser browse the term
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 PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.
Synonyms:exact_synonym: 8-bromoguanosine 3',5'-(hydrogen phosphate)
 related_synonym: 8-Br-Cyclic GMP;   8-Br-cGMP;   8-Bromo-cgmp;   8-Bromocyclic GMP;   8-Bromocyclic guanosine monophosphate;   8-Bromoguanosine 3',5'-cyclic monophosphate;   8-Bromoguanosine 3',5'-monophosphate;   Formula=C10H11BrN5O7P;   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
 xref: CAS:31356-94-2;   KEGG:C13817
 xref_mesh: MESH:C016276
 xref: PMID:10703694;   PMID:18509055;   PMID:18841072;   PMID:21918260;   Reaxys:1233440;   Wikipedia:8-Bromoguanosine_3'\,5'-cyclic_monophosphate


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8-bromo-3',5'-cyclic GMP term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Arhgef17 Rho guanine nucleotide exchange factor 17 multiple interactions ISO [8-bromocyclic GMP co-treated with PRKG1 protein co-treated with ARHGEF17 protein] results in increased activity of SRF protein CTD PMID:23195829 NCBI chr 1:155,230,607...155,290,581
Ensembl chr 1:155,233,168...155,290,498 		JBrowse link
G Casp3 caspase 3 multiple interactions ISO 8-bromocyclic GMP inhibits the reaction [TNF protein results in increased activity of CASP3 protein]; KT 5823 inhibits the reaction [8-bromocyclic GMP inhibits the reaction [TNF protein results in increased activity of CASP3 protein]] CTD PMID:9388267 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Cox4i1 cytochrome c oxidase subunit 4i1 increases expression
multiple interactions		 ISO 8-bromocyclic GMP results in increased expression of COX4I1 protein
tin protoporphyrin IX inhibits the reaction [8-bromocyclic GMP results in increased expression of COX4I1 protein]		 CTD PMID:24041027 NCBI chr19:48,721,680...48,727,920
Ensembl chr19:48,721,199...48,727,921 		JBrowse link
G Dusp10 dual specificity phosphatase 10 increases expression ISO 8-bromocyclic GMP results in increased expression of DUSP10 mRNA; 8-bromocyclic GMP results in increased expression of DUSP10 protein CTD PMID:29165873 NCBI chr13:95,613,716...95,651,716
Ensembl chr13:95,614,292...95,651,716 		JBrowse link
G Edn1 endothelin 1 multiple interactions EXP
ISO		 8-bromocyclic GMP inhibits the reaction [[EDN1 protein binds to and results in increased activity of EDNRB protein] which results in decreased activity of TH protein]
8-bromocyclic GMP inhibits the reaction [cobaltous chloride results in increased expression of EDN1 mRNA]; 8-bromocyclic GMP inhibits the reaction [cobaltous chloride results in increased expression of EDN1 protein]		 CTD PMID:16023617 PMID:29165873 NCBI chr17:22,454,924...22,460,812
Ensembl chr17:22,454,420...22,460,885 		JBrowse link
G Edn3 endothelin 3 multiple interactions EXP 8-bromocyclic GMP inhibits the reaction [[EDN3 protein binds to and results in increased activity of EDNRB protein] which results in decreased activity of TH protein] CTD PMID:16023617 NCBI chr 3:163,562,307...163,586,636
Ensembl chr 3:163,562,520...163,585,093 		JBrowse link
G Ednrb endothelin receptor type B multiple interactions EXP 8-bromocyclic GMP inhibits the reaction [[EDN1 protein binds to and results in increased activity of EDNRB protein] which results in decreased activity of TH protein]; 8-bromocyclic GMP inhibits the reaction [[EDN3 protein binds to and results in increased activity of EDNRB protein] which results in decreased activity of TH protein] CTD PMID:16023617 NCBI chr15:80,640,839...80,672,115
Ensembl chr15:80,643,043...80,672,115 		JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha multiple interactions ISO 8-bromocyclic GMP inhibits the reaction [cobaltous chloride results in increased expression of HIF1A mRNA]; 8-bromocyclic GMP inhibits the reaction [cobaltous chloride results in increased expression of HIF1A protein] CTD PMID:29165873 NCBI chr 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261 		JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO 8-bromocyclic GMP results in increased expression of HMOX1 mRNA; 8-bromocyclic GMP results in increased expression of HMOX1 protein CTD PMID:24041027 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO 8-bromocyclic GMP promotes the reaction [IL1B protein results in increased abundance of Nitrites]; Dipyridamole promotes the reaction [8-bromocyclic GMP promotes the reaction [IL1B protein results in increased abundance of Nitrites]] CTD PMID:8904084 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il4 interleukin 4 increases expression
multiple interactions		 ISO 8-bromocyclic GMP results in increased expression of IL4 mRNA
Cyclosporine inhibits the reaction [8-bromocyclic GMP results in increased expression of IL4 mRNA]		 CTD PMID:16533816 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 decreases phosphorylation ISO 8-bromocyclic GMP results in decreased phosphorylation of MAPK1 protein CTD PMID:17828804 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 decreases phosphorylation ISO 8-bromocyclic GMP results in decreased phosphorylation of MAPK3 protein CTD PMID:17828804 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases phosphorylation ISO 8-bromocyclic GMP results in decreased phosphorylation of MYC protein CTD PMID:17828804 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Ndufb8 NADH:ubiquinone oxidoreductase subunit B8 increases expression
multiple interactions		 ISO 8-bromocyclic GMP results in increased expression of NDUFB8 protein
tin protoporphyrin IX inhibits the reaction [8-bromocyclic GMP results in increased expression of NDUFB8 protein]		 CTD PMID:24041027 NCBI chr 1:243,408,659...243,413,701
Ensembl chr 1:243,408,619...243,413,817 		JBrowse link
G Nfatc1 nuclear factor of activated T-cells 1 affects localization ISO 8-bromocyclic GMP affects the localization of NFATC1 protein CTD PMID:16533816 NCBI chr18:74,046,421...74,156,041
Ensembl chr18:74,046,904...74,156,028 		JBrowse link
G Nrf1 nuclear respiratory factor 1 increases expression
multiple interactions		 ISO 8-bromocyclic GMP results in increased expression of NRF1 mRNA
tin protoporphyrin IX inhibits the reaction [8-bromocyclic GMP results in increased expression of NRF1 mRNA]		 CTD PMID:24041027 NCBI chr 4:58,664,932...58,772,328
Ensembl chr 4:58,664,957...58,825,328 		JBrowse link
G Pde5a phosphodiesterase 5A multiple interactions ISO [1-Methyl-3-isobutylxanthine co-treated with 8-bromocyclic GMP] results in increased expression of PDE5A protein; [1-Methyl-3-isobutylxanthine co-treated with 8-bromocyclic GMP] results in increased expression of PDE5A protein modified form CTD PMID:20613715 NCBI chr 2:210,858,515...211,003,480
Ensembl chr 2:210,858,063...210,999,701 		JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression
multiple interactions		 ISO 8-bromocyclic GMP results in increased expression of PPARGC1A mRNA
tin protoporphyrin IX inhibits the reaction [8-bromocyclic GMP results in increased expression of PPARGC1A mRNA]		 CTD PMID:24041027 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656 		JBrowse link
G Prkg1 protein kinase cGMP-dependent 1 increases expression
multiple interactions		 EXP
ISO		 8-bromocyclic GMP results in increased expression of PRKG1 protein
[8-bromocyclic GMP co-treated with PRKG1 protein co-treated with ARHGEF17 protein] results in increased activity of SRF protein		 CTD PMID:12620371 PMID:23195829 NCBI chr 1:228,409,883...229,638,794
Ensembl chr 1:228,408,947...229,639,080 		JBrowse link
G Scnn1b sodium channel epithelial 1 subunit beta multiple interactions ISO [1-Methyl-3-isobutylxanthine co-treated with 8-bromocyclic GMP] results in increased expression of SCNN1B protein CTD PMID:20613715 NCBI chr 1:176,430,063...176,484,451
Ensembl chr 1:176,430,103...176,484,451 		JBrowse link
G Sod2 superoxide dismutase 2 increases expression EXP 8-bromocyclic GMP results in increased expression of SOD2 mRNA; 8-bromocyclic GMP results in increased expression of SOD2 protein CTD PMID:14996425 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Spp1 secreted phosphoprotein 1 multiple interactions EXP 8-bromocyclic GMP inhibits the reaction [Glucose results in increased secretion of SPP1 protein]; Dinitrochlorobenzene inhibits the reaction [8-bromocyclic GMP inhibits the reaction [Glucose results in increased secretion of SPP1 protein]]; KT 5823 inhibits the reaction [8-bromocyclic GMP inhibits the reaction [Glucose results in increased secretion of SPP1 protein]]; N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide inhibits the reaction [8-bromocyclic GMP inhibits the reaction [Glucose results in increased secretion of SPP1 protein]] CTD PMID:20453393 NCBI chr14:5,308,885...5,315,120
Ensembl chr14:5,308,885...5,315,162 		JBrowse link
G Srf serum response factor multiple interactions ISO [8-bromocyclic GMP co-treated with PRKG1 protein co-treated with ARHGEF17 protein] results in increased activity of SRF protein CTD PMID:23195829 NCBI chr 9:14,426,453...14,435,734
Ensembl chr 9:14,426,472...14,435,733 		JBrowse link
G Tfam transcription factor A, mitochondrial increases expression
multiple interactions		 ISO 8-bromocyclic GMP results in increased expression of TFAM mRNA
tin protoporphyrin IX inhibits the reaction [8-bromocyclic GMP results in increased expression of TFAM mRNA]		 CTD PMID:24041027 NCBI chr20:17,356,243...17,368,293
Ensembl chr20:17,356,197...17,368,292 		JBrowse link
G Th tyrosine hydroxylase multiple interactions EXP 8-bromocyclic GMP inhibits the reaction [[EDN1 protein binds to and results in increased activity of EDNRB protein] which results in decreased activity of TH protein]; 8-bromocyclic GMP inhibits the reaction [[EDN3 protein binds to and results in increased activity of EDNRB protein] which results in decreased activity of TH protein] CTD PMID:16023617 NCBI chr 1:198,071,500...198,078,832
Ensembl chr 1:198,071,503...198,109,767 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO 8-bromocyclic GMP inhibits the reaction [TNF protein results in increased activity of CASP3 protein]; KT 5823 inhibits the reaction [8-bromocyclic GMP inhibits the reaction [TNF protein results in increased activity of CASP3 protein]] CTD PMID:9388267 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tp53 tumor protein p53 increases expression EXP 8-bromocyclic GMP results in increased expression of TP53 protein CTD PMID:9888876 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Trpc6 transient receptor potential cation channel, subfamily C, member 6 multiple interactions
increases phosphorylation		 EXP
ISO		 8-bromocyclic GMP inhibits the reaction [1-oleoyl-2-acetylglycerol results in increased activity of TRPC6 protein]
8-bromocyclic GMP results in increased phosphorylation of TRPC6 protein
KT 5823 inhibits the reaction [8-bromocyclic GMP results in increased phosphorylation of TRPC6 protein]		 CTD PMID:20177073 NCBI chr 8:5,759,387...5,864,000
Ensembl chr 8:5,758,935...5,828,092 		JBrowse link
G Txn1 thioredoxin 1 multiple interactions EXP 8-bromocyclic GMP inhibits the reaction [Glucose results in decreased expression of TXN1 protein] CTD PMID:20453393 NCBI chr 5:72,712,334...72,724,564
Ensembl chr 5:72,711,933...72,724,629 		JBrowse link
G Uqcrc1 ubiquinol-cytochrome c reductase core protein 1 multiple interactions
increases expression		 ISO tin protoporphyrin IX inhibits the reaction [8-bromocyclic GMP results in increased expression of UQCRC1 protein] CTD PMID:24041027 NCBI chr 8:109,589,735...109,601,481
Ensembl chr 8:109,589,706...109,601,480 		JBrowse link
G Vcam1 vascular cell adhesion molecule 1 decreases expression ISO 8-bromocyclic GMP results in decreased expression of VCAM1 protein CTD PMID:17828804 NCBI chr 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958 		JBrowse link
G Vegfa vascular endothelial growth factor A decreases expression ISO 8-bromocyclic GMP results in decreased expression of VEGFA protein CTD PMID:17828804 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
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                        oxygen atom 19666
                          oxygen molecular entity 19666
                            hydroxides 19412
                              oxoacid 18715
                                pnictogen oxoacid 11007
                                  phosphorus oxoacid 9812
                                    phosphoric acids 8640
                                      phosphoric acid 8640
                                        phosphoric acid derivative 8344
                                          phosphate 8344
                                            organic phosphate 8343
                                              carbohydrate phosphate 1831
                                                phospho sugar 1679
                                                  aldose phosphate 1677
                                                    aldopentose phosphate 1669
                                                      ribose phosphate 1664
                                                        ribonucleotide 1623
                                                          purine ribonucleotide 1596
                                                            guanyl ribonucleotide 140
                                                              3',5'-cyclic GMP 74
                                                                8-bromo-3',5'-cyclic GMP 33
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