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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:bicuculline
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Accession:CHEBI:3092 term browser browse the term
Definition:A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.
Synonyms:exact_synonym: (6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one
 related_synonym: Bicculine;   Bicucullin;   Formula=C20H17NO6;   InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1;   InChIKey=IYGYMKDQCDOMRE-ZWKOTPCHSA-N;   SMILES=[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@@]1([H])N(C)CCc2cc3OCOc3cc12;   d-Bicuculline
 xref: Beilstein:98786;   CAS:485-49-4;   KEGG:C09364;   KNApSAcK:C00001820
 xref_mesh: MESH:D001640
 xref: PMID:27579770;   PMID:29137474;   PMID:29949743;   PMID:30858801;   Wikipedia:Bicuculline


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bicuculline term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Arc activity-regulated cytoskeleton-associated protein multiple interactions EXP Bicuculline inhibits the reaction [Propofol results in decreased expression of ARC protein] CTD PMID:18946287 NCBI chr 7:106,555,968...106,559,697
Ensembl chr 7:106,555,785...106,559,378 		JBrowse link
G Casp3 caspase 3 multiple interactions ISO [Bicuculline co-treated with Ethanol] results in increased cleavage of CASP3 protein CTD PMID:29044621 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Creb1 cAMP responsive element binding protein 1 increases phosphorylation EXP Bicuculline results in increased phosphorylation of CREB1 protein CTD PMID:22534176 NCBI chr 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816 		JBrowse link
G Ern1 endoplasmic reticulum to nucleus signaling 1 multiple interactions ISO [Bicuculline co-treated with Ethanol] results in increased phosphorylation of ERN1 protein CTD PMID:29044621 NCBI chr10:91,326,889...91,421,201
Ensembl chr10:91,330,654...91,421,029 		JBrowse link
G Gabra1 gamma-aminobutyric acid type A receptor subunit alpha 1 multiple interactions
decreases expression		 EXP
ISO		 Bicuculline inhibits the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB1 protein]]; Bicuculline inhibits the reaction [methylmercuric chloride promotes the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB2 protein binds to GABRG2 protein]]]
Bicuculline results in decreased expression of GABRA1 mRNA
Bicuculline promotes the reaction [tetramethylenedisulfotetramine inhibits the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB2 protein binds to GABRG2 protein alternative form]]]; Bicuculline results in decreased activity of [GABRA1 protein binds to GABRB1 binds to GABRG2 protein alternative form]		 CTD PMID:1977069 PMID:9600394 PMID:27720918 PMID:29038840 NCBI chr10:26,595,151...26,650,611
Ensembl chr10:26,595,160...26,650,864 		JBrowse link
G Gabra2 gamma-aminobutyric acid type A receptor subunit alpha 2 multiple interactions ISO Bicuculline results in decreased activity of [GABRA2 protein binds to GABRB3 binds to GABRG2 protein alternative form] CTD PMID:29038840 NCBI chr14:37,097,251...37,230,030
Ensembl chr14:37,097,279...37,228,944 		JBrowse link
G Gabra6 gamma-aminobutyric acid type A receptor subunit alpha6 multiple interactions EXP
ISO		 Bicuculline inhibits the reaction [methylmercuric chloride promotes the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA6 protein binds to GABRB2 protein binds to GABRG2 protein]]]
Bicuculline results in decreased activity of [GABRA6 protein binds to GABRB1 binds to GABRG2 protein alternative form]; Bicuculline results in decreased activity of [GABRA6 protein binds to GABRB3 binds to GABRG2 protein alternative form]		 CTD PMID:27720918 PMID:29038840 NCBI chr10:26,810,411...26,825,768
Ensembl chr10:26,810,423...26,825,769 		JBrowse link
G Gabrb1 gamma-aminobutyric acid type A receptor subunit beta1 multiple interactions EXP
ISO		 Bicuculline inhibits the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB1 protein]]
Bicuculline results in decreased activity of [GABRA1 protein binds to GABRB1 binds to GABRG2 protein alternative form]; Bicuculline results in decreased activity of [GABRA6 protein binds to GABRB1 binds to GABRG2 protein alternative form]		 CTD PMID:1977069 PMID:29038840 NCBI chr14:36,068,725...36,548,946
Ensembl chr14:36,080,393...36,548,948 		JBrowse link
G Gabrb2 gamma-aminobutyric acid type A receptor subunit beta 2 multiple interactions EXP
ISO		 Bicuculline inhibits the reaction [methylmercuric chloride promotes the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB2 protein binds to GABRG2 protein]]]; Bicuculline inhibits the reaction [methylmercuric chloride promotes the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA6 protein binds to GABRB2 protein binds to GABRG2 protein]]]
Bicuculline promotes the reaction [tetramethylenedisulfotetramine inhibits the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB2 protein binds to GABRG2 protein alternative form]]]		 CTD PMID:27720918 PMID:29038840 NCBI chr10:26,936,592...27,156,141
Ensembl chr10:26,936,551...27,151,251 		JBrowse link
G Gabrb3 gamma-aminobutyric acid type A receptor subunit beta 3 decreases expression
multiple interactions		 EXP
ISO		 Bicuculline results in decreased expression of GABRB3 mRNA
Bicuculline results in decreased activity of [GABRA2 protein binds to GABRB3 binds to GABRG2 protein alternative form]; Bicuculline results in decreased activity of [GABRA6 protein binds to GABRB3 binds to GABRG2 protein alternative form]		 CTD PMID:9600394 PMID:29038840 NCBI chr 1:108,467,047...108,702,522
Ensembl chr 1:108,296,124...108,698,961 		JBrowse link
G Gabrg1 gamma-aminobutyric acid type A receptor subunit gamma 1 decreases expression EXP Bicuculline results in decreased expression of GABRG1 mRNA CTD PMID:9600394 NCBI chr14:37,396,217...37,469,606
Ensembl chr14:37,396,294...37,635,956 		JBrowse link
G Gabrg2 gamma-aminobutyric acid type A receptor subunit gamma 2 multiple interactions EXP
ISO		 Bicuculline inhibits the reaction [methylmercuric chloride promotes the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB2 protein binds to GABRG2 protein]]]; Bicuculline inhibits the reaction [methylmercuric chloride promotes the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA6 protein binds to GABRB2 protein binds to GABRG2 protein]]]
Bicuculline promotes the reaction [tetramethylenedisulfotetramine inhibits the reaction [gamma-Aminobutyric Acid results in increased activity of [GABRA1 protein binds to GABRB2 protein binds to GABRG2 protein alternative form]]]; Bicuculline results in decreased activity of [GABRA1 protein binds to GABRB1 binds to GABRG2 protein alternative form]; Bicuculline results in decreased activity of [GABRA2 protein binds to GABRB3 binds to GABRG2 protein alternative form]; Bicuculline results in decreased activity of [GABRA6 protein binds to GABRB1 binds to GABRG2 protein alternative form]; Bicuculline results in decreased activity of [GABRA6 protein binds to GABRB3 binds to GABRG2 protein alternative form]		 CTD PMID:27720918 PMID:29038840 NCBI chr10:26,374,693...26,463,937
Ensembl chr10:26,374,694...26,464,346 		JBrowse link
G Gnrh1 gonadotropin releasing hormone 1 multiple interactions EXP Bicuculline affects the reaction [bisphenol A affects the secretion of GNRH1 protein]; Bicuculline promotes the reaction [manganese chloride results in increased secretion of GNRH1 protein] CTD PMID:18603625 PMID:26950200 NCBI chr15:41,972,482...41,976,690
Ensembl chr15:41,972,905...41,973,581
Ensembl chr15:41,972,905...41,973,581 		JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions ISO Bicuculline promotes the reaction [Ethanol results in increased activity of GPT protein] CTD PMID:29044621 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494 		JBrowse link
G Gria1 glutamate ionotropic receptor AMPA type subunit 1 multiple interactions
decreases expression 		EXP Bicuculline results in decreased expression of and results in decreased localization of GRIA1 protein
Bicuculline decreases expression of Gria1 protein on nucleus accumbens medium spiny neurons		 CTD
RGD		 PMID:19674091 PMID:24712995 RGD:405650624 NCBI chr10:41,210,713...41,527,283
Ensembl chr10:41,210,713...41,527,283 		JBrowse link
G Gria2 glutamate ionotropic receptor AMPA type subunit 2 multiple interactions
decreases expression		 EXP
ISO		 Bicuculline promotes the reaction [MECP2 protein binds to GRIA2 promoter]; Bicuculline results in decreased expression of and results in decreased localization of GRIA2 protein; MECP2 protein affects the reaction [Bicuculline results in decreased expression of GRIA2 protein]
Bicuculline results in decreased expression of GRIA2 mRNA; Bicuculline results in decreased expression of GRIA2 protein		 CTD PMID:19674091 PMID:22262897 NCBI chr 2:165,949,379...166,069,510
Ensembl chr 2:165,947,521...166,069,510 		JBrowse link
G Grin2d glutamate ionotropic receptor NMDA type subunit 2D multiple interactions ISO [Bicuculline co-treated with 4-Aminopyridine] results in decreased expression of GRIN2D protein CTD PMID:19911010 NCBI chr 1:96,306,871...96,346,994
Ensembl chr 1:96,308,365...96,344,793 		JBrowse link
G Hdac5 histone deacetylase 5 multiple interactions EXP [Bicuculline co-treated with 4-Aminopyridine] affects the localization of HDAC5 protein CTD PMID:15773917 NCBI chr10:87,152,978...87,187,921
Ensembl chr10:87,152,978...87,188,235 		JBrowse link
G Map3k5 mitogen-activated protein kinase kinase kinase 5 multiple interactions ISO [Bicuculline co-treated with Ethanol] results in increased expression of MAP3K5 protein CTD PMID:29044621 NCBI chr 1:14,685,776...14,904,935
Ensembl chr 1:14,685,492...14,904,800 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions EXP
ISO		 Bicuculline inhibits the reaction [methyl tert-butyl ether results in decreased phosphorylation of MAPK1 protein]
[Bicuculline co-treated with 4-Aminopyridine] results in increased activity of and results in increased phosphorylation of MAPK1 protein; Dizocilpine Maleate inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] results in increased activity of and results in increased phosphorylation of MAPK1 protein]		 CTD PMID:19344668 PMID:19911010 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 multiple interactions EXP
ISO		 Bicuculline inhibits the reaction [methyl tert-butyl ether results in decreased phosphorylation of MAPK3 protein]
[Bicuculline co-treated with 4-Aminopyridine] results in increased activity of and results in increased phosphorylation of MAPK3 protein; Dizocilpine Maleate inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] results in increased activity of and results in increased phosphorylation of MAPK3 protein]		 CTD PMID:19344668 PMID:19911010 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions ISO [Bicuculline co-treated with Ethanol] results in increased expression of MAPK8 protein CTD PMID:29044621 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mecp2 methyl CpG binding protein 2 multiple interactions
increases expression
increases phosphorylation		 ISO
EXP		 MECP2 protein affects the reaction [Bicuculline results in decreased expression of GRIA2 protein]
Bicuculline results in increased expression of MECP2 mRNA
Bicuculline results in increased phosphorylation of MECP2 protein
Bicuculline promotes the reaction [MECP2 protein binds to GRIA2 promoter]; MECP2 protein affects the reaction [Bicuculline results in decreased expression of GRIA2 protein]		 CTD PMID:22262897 NCBI chr  X:151,781,177...151,844,687
Ensembl chr  X:151,789,930...151,844,689 		JBrowse link
G Mpdz multiple PDZ domain crumbs cell polarity complex component affects response to substance ISO MPDZ protein affects the susceptibility to Bicuculline CTD PMID:14960011 NCBI chr 5:95,766,112...95,920,531
Ensembl chr 5:95,766,118...95,920,499 		JBrowse link
G Ncor2 nuclear receptor co-repressor 2 multiple interactions EXP 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] affects the localization of NCOR2 protein]; [Bicuculline co-treated with 4-Aminopyridine] affects the localization of NCOR2 protein; KN 62 inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] affects the localization of NCOR2 protein]; STO 609 inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] affects the localization of NCOR2 protein] CTD PMID:15773917 NCBI chr12:31,466,418...31,628,319
Ensembl chr12:31,466,412...31,628,319 		JBrowse link
G Ngf nerve growth factor multiple interactions EXP Bicuculline inhibits the reaction [Propofol inhibits the reaction [Vincristine results in decreased susceptibility to NGF protein]]; Bicuculline inhibits the reaction [Thiopental inhibits the reaction [Vincristine results in decreased susceptibility to NGF protein]] CTD PMID:11991087 NCBI chr 2:189,901,058...189,954,452
Ensembl chr 2:189,901,058...189,954,452 		JBrowse link
G Oxtr oxytocin receptor multiple interactions EXP Bicuculline inhibits the reaction [oxytocin, Thr(4)-Gly(7)- results in increased activity of OXTR protein] CTD PMID:11069593 NCBI chr 4:145,598,549...145,614,674
Ensembl chr 4:145,599,561...145,614,674 		JBrowse link
G Rara retinoic acid receptor, alpha multiple interactions EXP [Bicuculline co-treated with 4-Aminopyridine] promotes the reaction [alitretinoin results in increased activity of RARA protein]; Dizocilpine Maleate inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] promotes the reaction [alitretinoin results in increased activity of RARA protein]]; KN 62 inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] promotes the reaction [alitretinoin results in increased activity of RARA protein]]; STO 609 inhibits the reaction [[Bicuculline co-treated with 4-Aminopyridine] promotes the reaction [alitretinoin results in increased activity of RARA protein]] CTD PMID:15773917 NCBI chr10:83,883,490...83,928,932
Ensembl chr10:83,893,384...83,928,142 		JBrowse link
G Ryr1 ryanodine receptor 1 increases response to substance EXP RYR1 results in increased susceptibility to Bicuculline CTD PMID:22534176 NCBI chr 1:84,292,578...84,423,824
Ensembl chr 1:84,292,578...84,423,812 		JBrowse link
G Ryr2 ryanodine receptor 2 increases response to substance EXP RYR2 results in increased susceptibility to Bicuculline CTD PMID:22534176 NCBI chr17:58,389,925...58,975,641
Ensembl chr17:58,389,925...58,975,142 		JBrowse link
G Th tyrosine hydroxylase multiple interactions EXP Bicuculline promotes the reaction [Reserpine affects the activity of TH protein]; Bicuculline promotes the reaction [Reserpine results in increased expression of TH mRNA] CTD PMID:1981253 NCBI chr 1:198,071,500...198,078,832
Ensembl chr 1:198,071,503...198,109,767 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19838
    role 19814
      application 19658
        agrochemical 16285
          bicuculline 31
Path 2
Term Annotations click to browse term
  CHEBI ontology 19838
    subatomic particle 19836
      composite particle 19836
        hadron 19836
          baryon 19836
            nucleon 19836
              atomic nucleus 19836
                atom 19836
                  main group element atom 19786
                    p-block element atom 19786
                      carbon group element atom 19734
                        carbon atom 19731
                          organic molecular entity 19731
                            heteroorganic entity 19488
                              organonitrogen compound 18810
                                alkaloid 7825
                                  isoquinoline alkaloid 1194
                                    benzylisoquinoline alkaloid 219
                                      bicuculline 31
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