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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 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
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 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
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 chr15:103,695,415...103,927,980
Ensembl chr15:103,696,557...103,927,592
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 4:88,765,441...88,890,268
Ensembl chr 4:88,832,178...88,890,621
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 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
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:135,304,063...135,343,062
Ensembl chr  X:135,304,066...135,343,087
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 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
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 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
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 chr18:56,337,485...56,355,477
Ensembl chr18:56,338,336...56,355,490
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 8:129,601,511...129,628,378
Ensembl chr 8:129,617,812...129,627,372
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 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
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 1:256,382,861...256,386,729
Ensembl chr 1:256,382,791...256,386,729
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:10,400,363...10,414,010
Ensembl chr  X:10,400,366...10,413,995
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 2:21,931,887...21,958,927
Ensembl chr 2:21,931,493...21,962,453
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 chr12:38,490,230...38,503,344
Ensembl chr12:38,490,230...38,503,330
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 1:82,097,244...82,108,238
Ensembl chr 1:82,097,247...82,108,203
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 chr11:65,060,884...65,208,842
Ensembl chr11:65,066,235...65,209,268
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 4:82,124,358...82,127,182
Ensembl chr 4:82,125,406...82,127,066
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 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
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 7:58,447,097...58,587,787
Ensembl chr 7:58,448,277...58,587,787
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 2:197,786,212...197,788,992 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 chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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 chr18:62,159,128...62,179,635
Ensembl chr18:62,174,670...62,181,102
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 chr20:3,747,231...3,751,994
Ensembl chr20:3,747,221...3,751,994
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
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 chr10:91,830,709...91,874,907
Ensembl chr10:91,830,654...91,874,793
JBrowse link

Term paths to the root
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  CHEBI ontology 19816
    chemical entity 19816
      atom 19814
        nonmetal atom 19690
          carbon atom 19597
            organic molecular entity 19597
              oxime 176
                ketoxime 100
                  6-bromoindirubin-3'-oxime 26
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        carboacyl group 17372
                                          univalent carboacyl group 17372
                                            carbamoyl group 17158
                                              carboxamide 17158
                                                lactam 8034
                                                  gamma-lactam 6269
                                                    oxindoles 5829
                                                      6-bromoindirubin-3'-oxime 26
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