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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:butein
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Accession:CHEBI:3237 term browser browse the term
Definition:A chalcone that is (E)-chalcone bearing four additional hydroxy substituents at positions 2', 3, 4 and 4'.
Synonyms:exact_synonym: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one;   (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
 related_synonym: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one;   (E)-2',3,4,4'-terahydroxychalcone;   2',3,4,4'-Tetrahydroxychalcone;   Formula=C15H12O5;   InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+;   InChIKey=AYMYWHCQALZEGT-ORCRQEGFSA-N;   SMILES=OC1=CC(O)=C(C=C1)C(=O)\\C=C\\C1=CC(O)=C(O)C=C1
 xref: CAS:487-52-5;   Chemspider:4444634;   FooDB:FDB000082;   KEGG:C08578;   KNApSAcK:C00006941;   LINCS:LSM-42896;   LIPID_MAPS_instance:LMPK12120111
 xref_mesh: MESH:C040918
 xref: MetaCyc:BUTEIN;   PDBeChem:BUN;   PMID:12939617;   PMID:19643530;   PMID:20515942;   PMID:20681544;   PMID:20696233;   PMID:20826149;   PMID:21131551;   PMID:21170936;   PMID:21212525;   PMID:21770460;   PMID:21964506;   PMID:22114764;   PMID:22155143;   PMID:22180353;   PMID:22185775;   PMID:22245810;   PMID:26081470;   PMID:29258953;   PMID:30344763;   PMID:31665136;   PMID:32033283;   PMID:32181410;   PMID:32325749;   PMID:32642916;   PMID:32663368;   PMID:33209079;   PMID:33294263;   PMID:33325610;   PMID:34271434;   PMID:34481015;   Reaxys:2056928;   Wikipedia:Butein


show annotations for term's descendants           Sort by:
butein term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G AKT1 AKT serine/threonine kinase 1 decreases phosphorylation
multiple interactions		 EXP butein results in decreased phosphorylation of AKT1 protein
Acetylcysteine inhibits the reaction [butein results in decreased phosphorylation of AKT1 protein]		 CTD PMID:20696233 PMID:35130734 NCBI chr14:104,769,349...104,795,748
Ensembl chr14:104,769,349...104,795,751 		JBrowse link
G BAX BCL2 associated X, apoptosis regulator increases expression ISO butein results in increased expression of BAX protein CTD PMID:11055382 NCBI chr19:48,954,875...48,961,798
Ensembl chr19:48,954,815...48,961,798 		JBrowse link
G BCL2 BCL2 apoptosis regulator decreases expression ISO butein results in decreased expression of BCL2 protein CTD PMID:11055382 NCBI chr18:63,123,346...63,320,090
Ensembl chr18:63,123,346...63,320,128 		JBrowse link
G BCL2L1 BCL2 like 1 decreases expression ISO butein results in decreased expression of BCL2L1 protein CTD PMID:11055382 NCBI chr20:31,664,452...31,723,963
Ensembl chr20:31,664,452...31,723,989 		JBrowse link
G CASP3 caspase 3 increases activity
multiple interactions		 EXP butein results in increased activity of CASP3 protein
Acetylcysteine inhibits the reaction [butein results in increased activity of CASP3 protein]		 CTD PMID:24931875 PMID:35130734 NCBI chr 4:184,627,696...184,649,447
Ensembl chr 4:184,627,696...184,650,062 		JBrowse link
G CASP8 caspase 8 increases activity EXP butein results in increased activity of CASP8 protein CTD PMID:35130734 NCBI chr 2:201,233,463...201,287,711
Ensembl chr 2:201,233,443...201,361,836 		JBrowse link
G CASP9 caspase 9 increases activity EXP butein results in increased activity of CASP9 protein CTD PMID:35130734 NCBI chr 1:15,491,401...15,524,912
Ensembl chr 1:15,490,832...15,526,534 		JBrowse link
G CDH1 cadherin 1 multiple interactions EXP butein affects the reaction [IL6 protein affects the expression of CDH1 protein] CTD PMID:35130734 NCBI chr16:68,737,292...68,835,537
Ensembl chr16:68,737,292...68,835,537 		JBrowse link
G DIO2 iodothyronine deiodinase 2 decreases activity EXP butein results in decreased activity of DIO2 protein CTD PMID:17327447 NCBI chr14:80,197,526...80,231,057
Ensembl chr14:80,197,526...80,387,757 		JBrowse link
G GPX4 glutathione peroxidase 4 decreases expression EXP butein results in decreased expression of GPX4 protein CTD PMID:35130734 NCBI chr19:1,103,994...1,106,779
Ensembl chr19:1,103,982...1,106,791 		JBrowse link
G HMOX1 heme oxygenase 1 multiple interactions EXP [butein results in increased expression of HMOX1 protein] inhibits the reaction [Hydrogen Peroxide results in increased abundance of Reactive Oxygen Species]; [butein results in increased expression of HMOX1 protein] which results in decreased susceptibility to Hydrogen Peroxide; [tin protoporphyrin IX results in decreased expression of and results in decreased activity of HMOX1 protein] inhibits the reaction [butein inhibits the reaction [Hydrogen Peroxide results in increased abundance of Reactive Oxygen Species]]; butein results in increased expression of and results in increased activity of HMOX1 protein; pyrazolanthrone inhibits the reaction [butein results in increased expression of HMOX1 protein] CTD PMID:23318726 NCBI chr22:35,381,096...35,394,207
Ensembl chr22:35,380,361...35,394,214 		JBrowse link
G IL6 interleukin 6 multiple interactions EXP butein affects the reaction [IL6 protein affects the expression of CDH1 protein]; butein affects the reaction [IL6 protein affects the expression of MMP2 protein]; butein affects the reaction [IL6 protein affects the expression of MMP9 protein]; butein affects the reaction [IL6 protein affects the phosphorylation of STAT3 protein] CTD PMID:35130734 NCBI chr 7:22,727,200...22,731,998
Ensembl chr 7:22,725,884...22,732,002 		JBrowse link
G MAP1LC3B microtubule associated protein 1 light chain 3 beta multiple interactions
increases lipidation		 EXP Acetylcysteine inhibits the reaction [butein results in increased lipidation of MAP1LC3B protein]; MK 2206 promotes the reaction [butein results in increased lipidation of MAP1LC3B protein]; pyrazolanthrone inhibits the reaction [butein results in increased lipidation of MAP1LC3B protein] CTD PMID:35130734 NCBI chr16:87,392,336...87,404,774
Ensembl chr16:87,383,953...87,404,779 		JBrowse link
G MAPK8 mitogen-activated protein kinase 8 multiple interactions
increases phosphorylation		 EXP Acetylcysteine inhibits the reaction [butein results in increased phosphorylation of MAPK8 protein] CTD PMID:35130734 NCBI chr10:48,306,677...48,439,360
Ensembl chr10:48,306,639...48,439,360 		JBrowse link
G MMP2 matrix metallopeptidase 2 multiple interactions EXP butein affects the reaction [IL6 protein affects the expression of MMP2 protein] CTD PMID:35130734 NCBI chr16:55,478,830...55,506,691
Ensembl chr16:55,389,700...55,506,691 		JBrowse link
G MMP9 matrix metallopeptidase 9 multiple interactions
decreases expression		 EXP 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one promotes the reaction [butein results in decreased expression of MMP9 protein]; benzyloxycarbonylleucyl-leucyl-leucine aldehyde promotes the reaction [butein results in decreased expression of MMP9 protein]; Bortezomib promotes the reaction [butein results in decreased expression of MMP9 protein]; butein affects the reaction [IL6 protein affects the expression of MMP9 protein]; butein inhibits the reaction [TNF protein results in increased expression of MMP9 protein]; prolinedithiocarbamate promotes the reaction [butein results in decreased expression of MMP9 protein]
butein results in decreased expression of MMP9 mRNA; butein results in decreased expression of MMP9 protein		 CTD PMID:20696233 PMID:35130734 NCBI chr20:46,008,908...46,016,561
Ensembl chr20:46,008,908...46,016,561 		JBrowse link
G MTOR mechanistic target of rapamycin kinase multiple interactions
decreases phosphorylation		 EXP Acetylcysteine inhibits the reaction [butein results in decreased phosphorylation of MTOR protein] CTD PMID:35130734 NCBI chr 1:11,106,535...11,262,551
Ensembl chr 1:11,106,535...11,262,556 		JBrowse link
G NFE2L2 NFE2 like bZIP transcription factor 2 affects localization EXP butein affects the localization of NFE2L2 protein CTD PMID:23318726 NCBI chr 2:177,230,303...177,264,727
Ensembl chr 2:177,218,667...177,392,756 		JBrowse link
G NFKB1 nuclear factor kappa B subunit 1 affects localization EXP butein affects the localization of NFKB1 protein CTD PMID:20696233 NCBI chr 4:102,501,359...102,617,302
Ensembl chr 4:102,501,330...102,617,302 		JBrowse link
G NR1I2 nuclear receptor subfamily 1 group I member 2 increases activity EXP butein results in increased activity of NR1I2 protein CTD PMID:29933105 NCBI chr 3:119,782,101...119,818,487
Ensembl chr 3:119,780,484...119,818,487 		JBrowse link
G PARP1 poly(ADP-ribose) polymerase 1 increases cleavage EXP butein results in increased cleavage of PARP1 protein CTD PMID:24931875 NCBI chr 1:226,360,691...226,408,093
Ensembl chr 1:226,360,210...226,408,154 		JBrowse link
G PTTG1 PTTG1 regulator of sister chromatid separation, securin decreases expression
decreases response to substance		 EXP butein results in decreased expression of PTTG1 protein
PTTG1 protein results in decreased susceptibility to butein		 CTD PMID:24931875 NCBI chr 5:160,421,855...160,428,744
Ensembl chr 5:160,421,855...160,428,739 		JBrowse link
G RELA RELA proto-oncogene, NF-kB subunit affects localization EXP butein affects the localization of RELA protein CTD PMID:20696233 NCBI chr11:65,653,601...65,663,857
Ensembl chr11:65,653,599...65,663,090 		JBrowse link
G SIRT1 sirtuin 1 increases activity EXP butein results in increased activity of SIRT1 protein CTD PMID:17327447 NCBI chr10:67,884,656...67,918,390
Ensembl chr10:67,884,656...67,918,390 		JBrowse link
G STAT3 signal transducer and activator of transcription 3 multiple interactions EXP butein affects the reaction [IL6 protein affects the phosphorylation of STAT3 protein] CTD PMID:35130734 NCBI chr17:42,313,324...42,388,442
Ensembl chr17:42,313,324...42,388,568 		JBrowse link
G TNF tumor necrosis factor multiple interactions EXP butein inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of TNF protein]; butein inhibits the reaction [TNF protein results in increased expression of MMP9 protein] CTD PMID:20696233 NCBI chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336 		JBrowse link
G VEGFA vascular endothelial growth factor A decreases expression EXP butein results in decreased expression of VEGFA mRNA CTD PMID:20696233 NCBI chr 6:43,770,211...43,786,487
Ensembl chr 6:43,770,184...43,786,487 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 26034
    role 25961
      chemical role 24242
        antioxidant 17487
          butein 27
Path 2
Term Annotations click to browse term
  CHEBI ontology 26034
    subatomic particle 26009
      composite particle 26009
        hadron 26020
          baryon 26009
            nucleon 26009
              atomic nucleus 26009
                atom 26009
                  main group element atom 25834
                    p-block element atom 25834
                      carbon group element atom 25434
                        carbon atom 25403
                          organic molecular entity 25392
                            heteroorganic entity 24766
                              organochalcogen compound 24378
                                organooxygen compound 24054
                                  carbonyl compound 23563
                                    ketone 19347
                                      alpha,beta-unsaturated ketone 10544
                                        enone 10544
                                          chalcones 1034
                                            butein 27
paths to the root