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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:gossypol
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Accession:CHEBI:28584 term browser browse the term
Definition:A polyphenol that has formula C30H30O8.
Synonyms:exact_synonym: 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)[2,2'-binaphthalene]-8,8'-dicarbaldehyde
 related_synonym: 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde;   1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-diisopropyl-2,2'-binaphthyl-8,8'-dialdehyde;   1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarboxaldehyde;   1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-8,8'-dicarbaldehyde;   1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarboxaldehyde;   2,2'-bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthyl];   2,2'-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthyl];   Formula=C30H30O8;   InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3;   InChIKey=QBKSWRVVCFFDOT-UHFFFAOYSA-N;   SMILES=[H]C(=O)C1=C(O)C(O)=C(C(C)C)C2=C1C(O)=C(C(C)=C2)C1=C(O)C2=C(C=C1C)C(C(C)C)=C(O)C(O)=C2C([H])=O;   gosipol
 alt_id: CHEBI:24427;   CHEBI:5526
 xref: CAS:303-45-7;   DrugBank:DB13044;   Drug_Central:1328;   FooDB:FDB000742;   KEGG:C07667;   KNApSAcK:C00003136;   LINCS:LSM-6229;   LIPID_MAPS_instance:LMPR0103330002
 xref_mesh: MESH:D006072
 xref: MetaCyc:CPD-9526;   PDBeChem:GO3;   PMID:36718333;   PMID:36928775;   PMID:37626472;   PMID:37763992;   PMID:37865884;   PMID:38098026;   PMID:38582865;   PMID:38632634;   PMID:38786676;   PMID:38786884;   PMID:38856661;   PMID:38864347;   PMID:38936520;   PMID:38960107;   Wikipedia:Gossypol


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gossypol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Alas1 5'-aminolevulinate synthase 1 multiple interactions
increases activity		 EXP chromium protoporphyrin IX promotes the reaction [Gossypol results in increased activity of ALAS1 protein] CTD PMID:15027808 NCBI chr 8:106,876,514...106,889,917
Ensembl chr 8:106,876,514...106,889,917 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions EXP
ISO		 [Gossypol co-treated with Methyltestosterone co-treated with Ethinyl Estradiol] results in increased expression of BAX mRNA
[gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in increased expression of BAX mRNA]		 CTD PMID:15451339 PMID:34699866 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bbc3 Bcl-2 binding component 3 increases expression ISO Gossypol results in increased expression of BBC3 protein CTD PMID:18840529 NCBI chr 1:77,013,281...77,022,509
Ensembl chr 1:77,014,543...77,022,509 		JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO [gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in decreased expression of BCL2 mRNA]; [gossypol acetic acid results in increased abundance of Gossypol] which results in decreased expression of BCL2 mRNA; ponatinib promotes the reaction [[gossypol acetic acid results in increased abundance of Gossypol] which results in decreased expression of BCL2 mRNA] CTD PMID:34699866 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Bcl2l1 Bcl2-like 1 multiple interactions
decreases expression		 ISO Gossypol analog binds to and affects the activity of BCL2L1 protein
Gossypol results in decreased expression of BCL2L1 protein		 CTD PMID:16020667 PMID:18840529 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479
Ensembl chr 1:141,253,523...141,303,479 		JBrowse link
G Bcl2l11 Bcl2-like 11 increases expression ISO Gossypol results in increased expression of BCL2L11 protein CTD PMID:18840529 NCBI chr 3:115,366,783...115,404,068
Ensembl chr 3:115,366,646...115,404,068 		JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 multiple interactions ISO [Gossypol results in decreased phosphorylation of EIF4EBP1 protein] inhibits the reaction [Epirubicin results in increased expression of BIRC5 protein]; Gossypol inhibits the reaction [Epirubicin results in increased expression of BIRC5 protein] CTD PMID:35872041 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380 		JBrowse link
G Casp3 caspase 3 multiple interactions
increases cleavage
increases activity		 ISO
EXP		 [zoledronic acid co-treated with Gossypol] results in increased activity of CASP3 protein
Gossypol results in increased cleavage of CASP3 protein
[Gossypol co-treated with Methyltestosterone co-treated with Ethinyl Estradiol] results in increased expression of CASP3 mRNA
Gossypol results in increased activity of CASP3 protein		 CTD PMID:15451339 PMID:18840529 PMID:19825521 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp7 caspase 7 multiple interactions
increases activity		 ISO [zoledronic acid co-treated with Gossypol] results in increased activity of CASP7 protein
Gossypol results in increased activity of CASP7 protein		 CTD PMID:19825521 NCBI chr 1:255,437,438...255,476,737
Ensembl chr 1:255,437,172...255,476,729 		JBrowse link
G Casp9 caspase 9 increases cleavage
multiple interactions		 ISO
EXP		 Gossypol results in increased cleavage of CASP9 protein
[gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in increased expression of CASP9 protein]; [gossypol acetic acid results in increased abundance of Gossypol] which results in increased expression of CASP9 protein; ponatinib promotes the reaction [[gossypol acetic acid results in increased abundance of Gossypol] which results in increased expression of CASP9 protein]
[Gossypol co-treated with Methyltestosterone co-treated with Ethinyl Estradiol] results in increased expression of CASP9 mRNA		 CTD PMID:15451339 PMID:18840529 PMID:34699866 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Cat catalase multiple interactions ISO [gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in increased activity of CAT protein]; [gossypol acetic acid results in increased abundance of Gossypol] which results in increased activity of CAT protein; ponatinib promotes the reaction [[gossypol acetic acid results in increased abundance of Gossypol] which results in increased activity of CAT protein] CTD PMID:34699866 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 decreases expression
multiple interactions		 ISO Gossypol results in decreased expression of CCL2 mRNA
zoledronic acid promotes the reaction [Gossypol results in decreased expression of CCL2 mRNA]		 CTD PMID:19825521 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Cdh2 cadherin 2 decreases expression EXP Gossypol results in decreased expression of CDH2 protein CTD PMID:15082077 NCBI chr18:7,776,704...7,990,934
Ensembl chr18:7,776,704...7,990,167 		JBrowse link
G Cxcl1 C-X-C motif chemokine ligand 1 multiple interactions ISO [zoledronic acid co-treated with Gossypol] results in decreased expression of CXCL1 mRNA CTD PMID:19825521 NCBI chr14:17,193,364...17,195,143
Ensembl chr14:17,193,365...17,195,215 		JBrowse link
G Cxcl3 C-X-C motif chemokine ligand 3 multiple interactions ISO [zoledronic acid co-treated with Gossypol] results in decreased expression of CXCL1 mRNA CTD PMID:19825521 NCBI chr14:17,287,727...17,289,451
Ensembl chr14:17,270,146...17,289,511 		JBrowse link
G Eif4ebp1 eukaryotic translation initiation factor 4E binding protein 1 multiple interactions ISO [Gossypol results in decreased phosphorylation of EIF4EBP1 protein] inhibits the reaction [Epirubicin results in increased expression of BIRC5 protein]; Gossypol inhibits the reaction [Epirubicin results in increased phosphorylation of EIF4EBP1 protein] CTD PMID:35872041 NCBI chr16:64,792,595...64,805,984
Ensembl chr16:64,790,226...64,805,984 		JBrowse link
G Ephb4 EPH receptor B4 multiple interactions ISO [zoledronic acid co-treated with Gossypol] results in decreased expression of EPHB4 mRNA CTD PMID:19825521 NCBI chr12:19,326,411...19,351,667
Ensembl chr12:19,326,427...19,351,314 		JBrowse link
G Fas Fas cell surface death receptor multiple interactions EXP [Gossypol co-treated with Methyltestosterone co-treated with Ethinyl Estradiol] results in increased expression of FAS mRNA CTD PMID:15451339 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591 		JBrowse link
G Fgf2 fibroblast growth factor 2 decreases expression
multiple interactions		 ISO Gossypol results in decreased expression of FGF2 mRNA
zoledronic acid promotes the reaction [Gossypol results in decreased expression of FGF2 mRNA]		 CTD PMID:19825521 NCBI chr 2:120,236,328...120,290,673
Ensembl chr 2:120,236,328...120,291,221 		JBrowse link
G Fgfr3 fibroblast growth factor receptor 3 decreases expression
multiple interactions		 ISO Gossypol results in decreased expression of FGFR3 mRNA
zoledronic acid promotes the reaction [Gossypol results in decreased expression of FGFR3 mRNA]		 CTD PMID:19825521 NCBI chr14:76,987,242...77,002,671
Ensembl chr14:76,987,993...77,003,341 		JBrowse link
G Fgfr4 fibroblast growth factor receptor 4 multiple interactions ISO [gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in decreased expression of FGFR4 mRNA]; [gossypol acetic acid results in increased abundance of Gossypol] which results in decreased expression of FGFR4 mRNA; ponatinib promotes the reaction [[gossypol acetic acid results in increased abundance of Gossypol] which results in decreased expression of FGFR4 mRNA] CTD PMID:34699866 NCBI chr17:9,461,541...9,476,268
Ensembl chr17:9,461,547...9,476,242 		JBrowse link
G Gja1 gap junction protein, alpha 1 decreases expression EXP Gossypol results in decreased expression of GJA1 protein CTD PMID:15082077 NCBI chr20:35,756,007...35,768,481
Ensembl chr20:35,755,991...35,768,582 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
increases activity		 EXP chromium protoporphyrin IX inhibits the reaction [Gossypol results in increased activity of HMOX1 protein] CTD PMID:15027808 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Hsd17b8 hydroxysteroid (17-beta) dehydrogenase 8 multiple interactions ISO [Gossypol co-treated with NAD] binds to HSD17B8 protein CTD PMID:25526675 NCBI chr20:4,826,725...4,828,742
Ensembl chr20:4,822,026...4,828,742 		JBrowse link
G Id1 inhibitor of DNA binding 1 decreases expression
multiple interactions		 ISO Gossypol results in decreased expression of ID1 mRNA
zoledronic acid promotes the reaction [Gossypol results in decreased expression of ID1 mRNA]		 CTD PMID:19825521 NCBI chr 3:141,210,666...141,212,420
Ensembl chr 3:141,211,267...141,212,419 		JBrowse link
G Lama5 laminin subunit alpha 5 multiple interactions ISO [zoledronic acid co-treated with Gossypol] results in decreased expression of LAMA5 mRNA CTD PMID:19825521 NCBI chr 3:167,270,296...167,318,370
Ensembl chr 3:167,270,296...167,318,451 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO Gossypol inhibits the reaction [Epirubicin results in increased phosphorylation of MAPK1 protein] CTD PMID:35872041 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 ISO Gossypol inhibits the reaction [Epirubicin results in increased phosphorylation of MAPK3 protein] CTD PMID:35872041 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression ISO Gossypol results in decreased expression of MCL1 protein CTD PMID:18840529 PMID:20587533 PMID:21750559 NCBI chr 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303 		JBrowse link
G Mdk midkine decreases expression
multiple interactions		 ISO Gossypol results in decreased expression of MDK mRNA
zoledronic acid promotes the reaction [Gossypol results in decreased expression of MDK mRNA]		 CTD PMID:19825521 NCBI chr 3:77,901,134...77,903,997
Ensembl chr 3:77,901,158...77,903,130 		JBrowse link
G Otc ornithine transcarbamylase multiple interactions EXP Gossypol inhibits the reaction [PRL protein results in increased activity of OTC protein]; Gossypol inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of OTC protein] CTD PMID:3097147 NCBI chr  X:12,453,834...12,529,954
Ensembl chr  X:12,453,834...12,566,918 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO [Gossypol co-treated with Epirubicin] results in increased cleavage of PARP1 protein CTD PMID:35872041 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Pdgfa platelet derived growth factor subunit A multiple interactions ISO [zoledronic acid co-treated with Gossypol] results in decreased expression of PDGFA mRNA CTD PMID:19825521 NCBI chr12:15,645,549...15,667,056
Ensembl chr12:15,645,541...15,666,497 		JBrowse link
G Prl prolactin multiple interactions EXP Gossypol inhibits the reaction [PRL protein results in increased activity of OTC protein] CTD PMID:3097147 NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062 		JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 multiple interactions ISO Gossypol inhibits the reaction [Epirubicin results in increased phosphorylation of RPS6KB1 protein] CTD PMID:35872041 NCBI chr10:71,323,777...71,367,908
Ensembl chr10:71,323,777...71,367,908 		JBrowse link
G Tp53 tumor protein p53 multiple interactions ISO [gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in increased expression of TRP53 protein]; [gossypol acetic acid results in increased abundance of Gossypol] which results in increased expression of TRP53 protein; ponatinib promotes the reaction [[gossypol acetic acid results in increased abundance of Gossypol] which results in increased expression of TRP53 protein] CTD PMID:34699866 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Tymp thymidine phosphorylase multiple interactions ISO Gossypol inhibits the reaction [zoledronic acid results in increased expression of TYMP mRNA] CTD PMID:19825521 NCBI chr 7:120,438,768...120,444,088
Ensembl chr 7:120,438,770...120,443,874
Ensembl chr 7:120,438,770...120,443,874 		JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions ISO [gossypol acetic acid results in increased abundance of Gossypol] promotes the reaction [ponatinib results in decreased expression of VEGFA protein]; [gossypol acetic acid results in increased abundance of Gossypol] which results in decreased expression of VEGFA protein; ponatinib promotes the reaction [[gossypol acetic acid results in increased abundance of Gossypol] which results in decreased expression of VEGFA protein] CTD PMID:34699866 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19874
    role 19844
      application 19689
        antispermatogenic agent 1163
          gossypol 38
Path 2
Term Annotations click to browse term
  CHEBI ontology 19874
    subatomic particle 19872
      composite particle 19872
        hadron 19872
          baryon 19872
            nucleon 19872
              atomic nucleus 19872
                atom 19872
                  main group element atom 19811
                    p-block element atom 19811
                      carbon group element atom 19751
                        carbon atom 19748
                          organic molecular entity 19748
                            heteroorganic entity 19505
                              organochalcogen compound 19268
                                organooxygen compound 19184
                                  carbon oxoacid 18654
                                    carboxylic acid 18651
                                      carboacyl group 17694
                                        univalent carboacyl group 17694
                                          formyl group 9051
                                            aldehyde 9051
                                              gossypol 38
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