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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:6-bromoindirubin-3'-oxime
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Accession:CHEBI:86290 term browser browse the term
Definition:A member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.
Synonyms:exact_synonym: (3Z)-6-bromo-3-[(3E)-3-(hydroxyimino)-1,3-dihydro-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one
 related_synonym: (2Z,3E)-6'-bromo-2,3'-biindole-2',3(1H,1'H)-dione 3-oxime;   (2Z,3E)-6-Bromoindirubin-3'-oxime;   6-BIO;   Formula=C16H10BrN3O2;   InChI=1S/C16H10BrN3O2/c17-8-5-6-9-12(7-8)19-16(21)13(9)15-14(20-22)10-3-1-2-4-11(10)18-15/h1-7,18,22H,(H,19,21)/b15-13-,20-14+;   InChIKey=DDLZLOKCJHBUHD-WAVHTBQISA-N;   SMILES=O\\N=C1\\C(\\Nc2ccccc\\12)=C1\\C(=O)Nc2cc(Br)ccc12
 alt_id: CHEBI:47271;   MESH:C483321
 xref_mesh: MESH:C483321
 xref: PDBeChem:BRW;   PMID:25130776;   PMID:25329250;   PMID:25437011;   PMID:25592083;   PMID:25727520;   PMID:25869056;   Reaxys:9653830


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6-bromoindirubin-3'-oxime term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions
increases expression
ISO
EXP
6-bromoindirubin-3'-oxime results in increased expression of and results in increased activity of ABCB1 protein
6-bromoindirubin-3'-oxime results in increased expression of ABCB1 mRNA
6-bromoindirubin-3'-oxime results in increased expression of ABCB1A mRNA; 6-bromoindirubin-3'-oxime results in increased expression of ABCB1A protein
CTD PMID:18624906 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 increases expression ISO 6-bromoindirubin-3'-oxime results in increased expression of ABCC2 mRNA; 6-bromoindirubin-3'-oxime results in increased expression of ABCC2 protein CTD PMID:18624906 NCBI chr 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238
JBrowse link
G Abcc4 ATP binding cassette subfamily C member 4 increases expression ISO 6-bromoindirubin-3'-oxime results in increased expression of ABCC4 mRNA; 6-bromoindirubin-3'-oxime results in increased expression of ABCC4 protein CTD PMID:18624906 NCBI chr15:95,541,186...95,774,898
Ensembl chr15:95,542,315...95,774,283
JBrowse link
G Abcg2 ATP binding cassette subfamily G member 2 increases expression ISO 6-bromoindirubin-3'-oxime results in increased expression of ABCG2 mRNA; 6-bromoindirubin-3'-oxime results in increased expression of ABCG2 protein CTD PMID:18624906 NCBI chr 4:87,676,241...87,802,757
Ensembl chr 4:87,745,319...87,802,409
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions ISO 6-bromoindirubin-3'-oxime binds to and results in increased activity of AHR protein CTD PMID:26259606 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G Aifm1 apoptosis inducing factor, mitochondria associated 1 multiple interactions ISO [sorafenib co-treated with 6-bromoindirubin-3'-oxime] affects the localization of AIFM1 protein CTD PMID:17991738 NCBI chr  X:127,650,223...127,689,356
Ensembl chr  X:127,650,226...127,689,256
JBrowse link
G Casp8 caspase 8 multiple interactions ISO 6-bromoindirubin-3'-oxime promotes the reaction [Paraquat results in increased expression of CASP8 protein modified form] CTD PMID:28414160 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Ccnd1 cyclin D1 increases expression ISO
EXP
6-bromoindirubin-3'-oxime results in increased expression of CCND1 mRNA CTD PMID:18624906 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
JBrowse link
G Cdx1 caudal type homeo box 1 multiple interactions ISO [Valproic Acid co-treated with 6-bromoindirubin-3'-oxime] results in increased expression of CDX1 mRNA CTD PMID:27693483 NCBI chr18:54,472,448...54,499,799
Ensembl chr18:54,473,444...54,490,814
JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions
increases expression
decreases phosphorylation
ISO [6-bromoindirubin-3'-oxime co-treated with DHFR mRNA] affects the expression of CTNNB1 protein; broussochalcone A inhibits the reaction [6-bromoindirubin-3'-oxime results in increased expression of CTNNB1 protein]; Methotrexate promotes the reaction [6-bromoindirubin-3'-oxime results in decreased phosphorylation of CTNNB1 protein] CTD PMID:18624906 PMID:19727391 PMID:26259606 PMID:31163223 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases expression
multiple interactions
ISO 6-bromoindirubin-3'-oxime results in increased expression of CYP1A2 mRNA
6-bromoindirubin-3'-oxime results in increased expression of and results in increased activity of CYP1A2 protein
CTD PMID:26259606 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp26a1 cytochrome P450, family 26, subfamily a, polypeptide 1 multiple interactions ISO [Valproic Acid co-treated with 6-bromoindirubin-3'-oxime] affects the expression of CYP26A1 mRNA CTD PMID:27693483 NCBI chr 1:235,471,368...235,475,204
Ensembl chr 1:235,471,298...235,475,204
JBrowse link
G Ddx3x DEAD-box helicase 3, X-linked multiple interactions ISO 6-bromoindirubin-3'-oxime promotes the reaction [Paraquat inhibits the reaction [TNFRSF10B protein binds to DDX3X protein]]; 6-bromoindirubin-3'-oxime promotes the reaction [Paraquat results in decreased expression of DDX3X protein modified form] CTD PMID:28414160 NCBI chr  X:9,479,532...9,493,455
Ensembl chr  X:9,479,532...9,493,168
JBrowse link
G Dhfr dihydrofolate reductase multiple interactions ISO [6-bromoindirubin-3'-oxime co-treated with DHFR mRNA] affects the expression of CTNNB1 protein CTD PMID:19727391 NCBI chr 2:23,585,876...23,611,199
Ensembl chr 2:23,586,031...23,613,713
JBrowse link
G Diablo diablo, IAP-binding mitochondrial protein multiple interactions ISO 6-bromoindirubin-3'-oxime promotes the reaction [sorafenib affects the localization of DIABLO protein] CTD PMID:17991738 NCBI chr12:33,055,784...33,070,400
Ensembl chr12:33,055,263...33,070,387
JBrowse link
G Gsk3a glycogen synthase kinase 3 alpha multiple interactions ISO 6-bromoindirubin-3'-oxime promotes the reaction [Paraquat results in decreased expression of GSK3A protein modified form] CTD PMID:28414160 NCBI chr 1:80,815,843...80,825,732
Ensembl chr 1:80,815,850...80,825,802
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta decreases activity
multiple interactions
increases phosphorylation
ISO 6-bromoindirubin-3'-oxime results in decreased activity of GSK3B protein
6-bromoindirubin-3'-oxime promotes the reaction [Paraquat inhibits the reaction [TNFRSF10B protein binds to GSK3B protein]]; 6-bromoindirubin-3'-oxime promotes the reaction [Paraquat results in decreased expression of GSK3B protein modified form]; Methotrexate promotes the reaction [6-bromoindirubin-3'-oxime results in increased phosphorylation of GSK3B protein]
CTD PMID:17991738 PMID:19727391 PMID:28414160 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646
JBrowse link
G Hoxa1 homeobox A1 multiple interactions ISO [Valproic Acid co-treated with 6-bromoindirubin-3'-oxime] affects the expression of HOXA1 mRNA CTD PMID:27693483 NCBI chr 4:81,255,814...81,258,504
Ensembl chr 4:81,255,883...81,258,504
JBrowse link
G Il6 interleukin 6 multiple interactions ISO [6-bromoindirubin-3'-oxime co-treated with Methotrexate] inhibits the reaction [Lipopolysaccharides results in increased secretion of IL6 protein] CTD PMID:19727391 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Lgr5 leucine rich repeat containing G protein coupled receptor 5 increases expression ISO 6-bromoindirubin-3'-oxime results in increased expression of LGR5 mRNA CTD PMID:26259606 NCBI chr 7:51,087,059...51,221,882
Ensembl chr 7:51,088,239...51,222,446
JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression ISO 6-bromoindirubin-3'-oxime results in decreased expression of MCL1 protein CTD PMID:17991738 NCBI chr 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO 6-bromoindirubin-3'-oxime promotes the reaction [Paraquat results in increased expression of PARP1 protein modified form] CTD PMID:28414160 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Pmaip1 phorbol-12-myristate-13-acetate-induced protein 1 multiple interactions ISO 6-bromoindirubin-3'-oxime inhibits the reaction [sorafenib results in decreased expression of PMAIP1 protein] CTD PMID:17991738 NCBI chr18:59,986,187...59,990,174
Ensembl chr18:59,986,017...59,992,429
JBrowse link
G Pou5f1 POU class 5 homeobox 1 multiple interactions ISO [Valproic Acid co-treated with 6-bromoindirubin-3'-oxime] results in decreased expression of POU5F1 mRNA CTD PMID:27693483 NCBI chr20:3,223,128...3,227,891
Ensembl chr20:3,223,129...3,227,891
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO [6-bromoindirubin-3'-oxime co-treated with Methotrexate] inhibits the reaction [Lipopolysaccharides results in increased secretion of TNF protein] CTD PMID:19727391 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Wnt3 Wnt family member 3 multiple interactions ISO [Valproic Acid co-treated with 6-bromoindirubin-3'-oxime] results in decreased expression of WNT3 mRNA CTD PMID:27693483 NCBI chr10:88,680,248...88,724,170
Ensembl chr10:88,680,248...88,724,099
JBrowse link

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  CHEBI ontology 19812
    chemical entity 19812
      atom 19811
        nonmetal atom 19698
          carbon atom 19620
            organic molecular entity 19620
              oxime 183
                ketoxime 105
                  6-bromoindirubin-3'-oxime 26
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  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19708
                    p-block element atom 19708
                      carbon group element atom 19630
                        carbon atom 19620
                          organic molecular entity 19620
                            organic group 18728
                              organic divalent group 18719
                                organodiyl group 18719
                                  carbonyl group 18667
                                    carbonyl compound 18667
                                      carboxylic acid 18364
                                        carboacyl group 17482
                                          univalent carboacyl group 17482
                                            carbamoyl group 17298
                                              carboxamide 17298
                                                lactam 8302
                                                  gamma-lactam 6585
                                                    oxindoles 5836
                                                      6-bromoindirubin-3'-oxime 26
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