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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:brucine
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Accession:CHEBI:3193 term browser browse the term
Definition:A monoterpenoid indole alkaloid that has formula C23H26N2O4.
Synonyms:related_synonym: Formula=C23H26N2O4;   InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1;   InChIKey=RRKTZKIUPZVBMF-IBTVXLQLSA-N;   SMILES=COc1cc2N3[C@H]4[C@@H]5[C@H](CC3=O)OCC=C3CN6CC[C@]4([C@@H]6C[C@H]53)c2cc1OC
 xref: CAS:357-57-3;   KEGG:C09084;   KNApSAcK:C00001695;   LINCS:LSM-5758
 xref_mesh: MESH:C083806
 xref: PPDB:3151

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brucine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Afp alpha-fetoprotein multiple interactions EXP brucine inhibits the reaction [Diethylnitrosamine results in increased expression of AFP protein] CTD PMID:24060683 NCBI chr14:19,141,755...19,159,919
Ensembl chr14:19,141,755...19,159,923 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO brucine results in increased expression of BAX protein CTD PMID:16443926 PMID:21684292 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO brucine results in decreased expression of BCL2 protein CTD PMID:16443926 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374 		JBrowse link
G Casp3 caspase 3 increases activity
increases expression
multiple interactions		 ISO [brucine results in increased activity of CASP9 protein] which results in increased activity of CASP3 protein; brucine results in increased activity of CASP3 protein
brucine results in increased expression of CASP3 protein
brucine results in increased expression of and results in increased activity of CASP3 protein; Cyclosporine inhibits the reaction [[brucine results in increased activity of CASP9 protein] which results in increased activity of CASP3 protein]		 CTD PMID:16442763 PMID:16443926 PMID:17449162 PMID:21684292 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204 		JBrowse link
G Casp9 caspase 9 multiple interactions
increases activity		 ISO brucine results in increased activity of and results in increased cleavage of CASP9 protein; Cyclosporine inhibits the reaction [[brucine results in increased activity of CASP9 protein] which results in increased activity of CASP3 protein]; Cyclosporine inhibits the reaction [brucine results in increased activity of and results in increased cleavage of CASP9 protein]
[brucine results in increased activity of CASP9 protein] which results in increased activity of CASP3 protein; brucine results in increased activity of CASP9 protein		 CTD PMID:16443926 PMID:21684292 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778 		JBrowse link
G Cat catalase multiple interactions EXP brucine inhibits the reaction [Diethylnitrosamine results in decreased activity of CAT protein] CTD PMID:24060683 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058 		JBrowse link
G Chrm1 cholinergic receptor, muscarinic 1 multiple interactions ISO brucine affects the reaction [muscarinic toxin 7 binds to CHRM1 protein]; brucine affects the reaction [Pirenzepine analog binds to CHRM1 protein]; brucine analog affects the reaction [Acetylcholine binds to CHRM1 protein]; brucine analog affects the reaction [N-Methylscopolamine binds to CHRM1 protein]; brucine promotes the reaction [(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride binds to CHRM1 protein]; brucine promotes the reaction [5-methylfurtrethonium binds to CHRM1 protein]; brucine promotes the reaction [Acetylcholine binds to CHRM1 protein]; brucine promotes the reaction [Acetylcholine results in increased activity of CHRM1 protein]; brucine promotes the reaction [Bethanechol binds to CHRM1 protein]; brucine promotes the reaction [Carbachol binds to CHRM1 protein]; brucine promotes the reaction [furtrethonium binds to CHRM1 protein]; brucine promotes the reaction [oxotremorine M binds to CHRM1 protein]; brucine promotes the reaction [Pilocarpine binds to CHRM1 protein]; Quinuclidinyl Benzilate inhibits the reaction [brucine promotes the reaction [Acetylcholine results in increased activity of CHRM1 protein]] CTD PMID:9224827 PMID:9495826 PMID:10069518 PMID:10101037 PMID:15294002 PMID:16439611 NCBI chr 1:224,869,087...224,885,101
Ensembl chr 1:224,882,439...224,884,205 		JBrowse link
G Chrm2 cholinergic receptor, muscarinic 2 multiple interactions
affects binding		 ISO brucine analog affects the reaction [Acetylcholine binds to CHRM2 protein]; brucine analog affects the reaction [N-Methylscopolamine binds to CHRM2 protein]; brucine promotes the reaction [N-Methylscopolamine binds to CHRM2 protein]
brucine binds to CHRM2 protein		 CTD PMID:9495826 PMID:10069518 PMID:15647330 NCBI chr 4:64,089,028...64,091,090
Ensembl chr 4:64,088,900...64,091,090 		JBrowse link
G Chrm3 cholinergic receptor, muscarinic 3 multiple interactions
affects binding		 ISO brucine analog affects the reaction [Acetylcholine binds to CHRM3 protein]; brucine analog affects the reaction [N-Methylscopolamine binds to CHRM3 protein]; brucine binds to and results in increased activity of CHRM3 protein mutant form; brucine promotes the reaction [(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride binds to CHRM3 protein]; brucine promotes the reaction [5-methylfurtrethonium binds to CHRM3 protein]; brucine promotes the reaction [Acetylcholine binds to CHRM3 protein]; brucine promotes the reaction [Arecoline binds to CHRM3 protein]; brucine promotes the reaction [Bethanechol binds to CHRM3 protein]; brucine promotes the reaction [Carbachol binds to CHRM3 protein]; brucine promotes the reaction [Carbachol results in increased activity of CHRM3 protein mutant form]; brucine promotes the reaction [furtrethonium binds to CHRM3 protein]; brucine promotes the reaction [oxotremorine M binds to CHRM3 protein]; brucine promotes the reaction [Pilocarpine binds to CHRM3 protein]
brucine binds to CHRM3 protein		 CTD PMID:9224827 PMID:10069518 PMID:15647330 PMID:20466821 NCBI chr17:63,990,599...64,463,222
Ensembl chr17:63,990,599...63,994,169 		JBrowse link
G Chrm4 cholinergic receptor, muscarinic 4 multiple interactions
affects binding		 ISO brucine analog affects the reaction [Acetylcholine binds to CHRM4 protein]; brucine analog affects the reaction [N-Methylscopolamine binds to CHRM4 protein]; brucine promotes the reaction [(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride binds to CHRM4 protein]; brucine promotes the reaction [5-methylfurtrethonium binds to CHRM4 protein]; brucine promotes the reaction [Bethanechol binds to CHRM4 protein]; brucine promotes the reaction [Carbachol binds to CHRM4 protein]; brucine promotes the reaction [furtrethonium binds to CHRM4 protein]; brucine promotes the reaction [oxotremorine M binds to CHRM4 protein]; brucine promotes the reaction [Pilocarpine binds to CHRM4 protein]; WIN 62577 inhibits the reaction [brucine binds to CHRM4 protein] CTD PMID:9224827 PMID:10069518 PMID:16709648 NCBI chr 3:80,833,272...80,841,165
Ensembl chr 3:80,833,272...80,841,006 		JBrowse link
G Ctsd cathepsin D decreases expression ISO brucine results in decreased expression of CTSD mRNA
brucine results in decreased expression of CTSD mRNA; brucine results in decreased expression of CTSD protein		 CTD PMID:23933019 NCBI chr 1:215,541,570...215,553,446
Ensembl chr 1:215,541,542...215,553,451 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 multiple interactions EXP [brucine co-treated with Glycyrrhetinic Acid] results in decreased activity of CYP1A2 protein CTD PMID:21800547 NCBI chr 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301 		JBrowse link
G Cyp2b1 cytochrome P450, family 2, subfamily b, polypeptide 1 increases expression EXP brucine results in increased expression of CYP2B1 protein CTD PMID:7906730 NCBI chr 7:99,142,431...99,183,540
Ensembl chr 7:99,142,450...99,181,783 		JBrowse link
G Cyp2b2 cytochrome P450, family 2, subfamily b, polypeptide 2 increases expression EXP brucine results in increased expression of CYP2B2 protein CTD PMID:7906730 NCBI chr 1:83,103,925...83,119,578
Ensembl chr 1:83,103,925...83,119,193 		JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 increases expression EXP brucine results in increased expression of CYP2B3 protein CTD PMID:8850324 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615 		JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions
increases activity		 EXP [brucine co-treated with Glycyrrhetinic Acid] results in decreased activity of CYP2E1 protein; [brucine co-treated with liquiritin] results in decreased activity of CYP2E1 protein
brucine results in increased activity of CYP2E1 protein		 CTD PMID:21800547 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542 		JBrowse link
G Fn1 fibronectin 1 decreases expression ISO brucine results in decreased expression of FN1 mRNA
brucine results in decreased expression of FN1 mRNA; brucine results in decreased expression of FN1 protein		 CTD PMID:23933019 NCBI chr 9:78,900,111...78,969,018
Ensembl chr 9:78,900,103...78,969,078 		JBrowse link
G Glra1 glycine receptor, alpha 1 multiple interactions ISO brucine analog binds to and results in decreased activity of GLRA1 protein; brucine binds to and results in decreased activity of GLRA1 protein CTD PMID:15081878 PMID:16687139 NCBI chr10:40,851,955...40,954,364
Ensembl chr10:40,855,559...40,953,651 		JBrowse link
G Gpt glutamic--pyruvic transaminase increases expression ISO brucine results in increased expression of GPT protein CTD PMID:31284022 NCBI chr 7:117,759,083...117,761,932
Ensembl chr 7:117,759,083...117,761,931 		JBrowse link
G Lox lysyl oxidase decreases expression ISO brucine results in decreased expression of LOX mRNA
brucine results in decreased expression of LOX mRNA; brucine results in decreased expression of LOX protein		 CTD PMID:23933019 NCBI chr18:47,500,320...47,577,819
Ensembl chr18:47,500,330...47,577,819 		JBrowse link
G Mbp myelin basic protein affects expression EXP brucine affects the expression of MBP mRNA CTD PMID:22954530 NCBI chr18:79,326,738...79,437,310
Ensembl chr18:79,326,738...79,437,310 		JBrowse link
G Mmp2 matrix metallopeptidase 2 decreases expression ISO brucine results in decreased expression of MMP2 mRNA
brucine results in decreased expression of MMP2 mRNA; brucine results in decreased expression of MMP2 protein		 CTD PMID:23933019 NCBI chr19:15,542,771...15,570,589
Ensembl chr19:15,542,765...15,570,611 		JBrowse link
G Npas2 neuronal PAS domain protein 2 multiple interactions ISO NPAS2 protein affects the metabolism of and affects the susceptibility to brucine CTD PMID:31284022 NCBI chr 9:45,901,262...46,081,880
Ensembl chr 9:45,901,741...46,081,880 		JBrowse link
G Pcna proliferating cell nuclear antigen multiple interactions EXP brucine inhibits the reaction [Diethylnitrosamine results in increased expression of PCNA protein] CTD PMID:24060683 NCBI chr 3:124,880,698...124,884,570
Ensembl chr 3:124,880,698...124,884,570 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO brucine results in decreased expression of PTGS2 protein CTD PMID:16442763 PMID:17449162 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335 		JBrowse link
G Tnf tumor necrosis factor decreases secretion ISO brucine results in decreased secretion of TNF protein CTD PMID:21684292 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
Ensembl chr20:5,189,390...5,192,000 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19761
    role 19711
      biological role 19711
        biochemical role 19301
          metabolite 19282
            alkaloid 5624
              indole alkaloid 1853
                terpenoid indole alkaloid 1473
                  monoterpenoid indole alkaloid 1463
                    brucine 26
                      5-oxobrucine 0
                      pseudobrucine 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19761
    subatomic particle 19759
      composite particle 19759
        hadron 19759
          baryon 19759
            nucleon 19759
              atomic nucleus 19759
                atom 19759
                  main group element atom 19653
                    p-block element atom 19653
                      carbon group element atom 19569
                        carbon atom 19559
                          organic molecular entity 19559
                            organic group 18593
                              cyclic organic group 1853
                                organic heterobicyclic ring 1853
                                  indole skeleton 1853
                                    indole alkaloid 1853
                                      terpenoid indole alkaloid 1473
                                        monoterpenoid indole alkaloid 1463
                                          brucine 26
                                            5-oxobrucine 0
                                            pseudobrucine 0
paths to the root