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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 		ISO 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 chr 6:137,534,810...137,555,131
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO butein results in increased expression of BAX protein CTD PMID:11055382 NCBI chr 1:105,076,472...105,081,906
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO butein results in decreased expression of BCL2 protein CTD PMID:11055382 NCBI chr13:23,204,464...23,366,900
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Bcl2l1 Bcl2-like 1 decreases expression ISO butein results in decreased expression of BCL2L1 protein CTD PMID:11055382 NCBI chr 3:161,713,777...161,764,844
Ensembl chr 3:141,253,523...141,303,479
Ensembl chr 1:141,253,523...141,303,479 		JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions 		ISO 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 chr16:52,395,539...52,413,794
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp8 caspase 8 increases activity ISO butein results in increased activity of CASP8 protein CTD PMID:35130734 NCBI chr 9:67,747,109...67,806,699
Ensembl chr 9:60,264,075...60,312,542 		JBrowse link
G Casp9 caspase 9 increases activity ISO butein results in increased activity of CASP9 protein CTD PMID:35130734 Ensembl chr 5:154,109,046...154,126,626 JBrowse link
G Cdh1 cadherin 1 multiple interactions ISO butein affects the reaction [IL6 protein affects the expression of CDH1 protein] CTD PMID:35130734 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775 		JBrowse link
G Dio2 iodothyronine deiodinase 2 decreases activity ISO butein results in decreased activity of DIO2 protein CTD PMID:17327447 NCBI chr 6:109,665,523...109,679,809
Ensembl chr 6:109,665,523...109,679,809 		JBrowse link
G Gpx4 glutathione peroxidase 4 decreases expression ISO butein results in decreased expression of GPX4 protein CTD PMID:35130734 NCBI chr 7:9,650,186...9,652,982
Ensembl chr 7:9,650,185...9,652,982 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions ISO [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 chr19:13,452,365...13,479,823
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Il6 interleukin 6 multiple interactions ISO 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 4:5,889,999...5,894,575
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Map1lc3b microtubule-associated protein 1 light chain 3 beta multiple interactions
increases lipidation 		ISO 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 chr19:66,571,631...66,582,270
Ensembl chr19:49,665,791...49,677,690
Ensembl chr16:49,665,791...49,677,690 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 increases phosphorylation
multiple interactions 		ISO butein results in increased phosphorylation of MAPK8 protein
Acetylcysteine inhibits the reaction [butein results in increased phosphorylation of MAPK8 protein] 		CTD PMID:35130734 NCBI chr16:8,645,171...8,728,225
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions ISO butein affects the reaction [IL6 protein affects the expression of MMP2 protein] CTD PMID:35130734 NCBI chr19:30,327,643...30,355,856
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions
decreases expression 		ISO 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 chr 3:174,103,474...174,111,434
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Mtor mechanistic target of rapamycin kinase decreases phosphorylation
multiple interactions 		ISO butein results in decreased phosphorylation of MTOR protein
Acetylcysteine inhibits the reaction [butein results in decreased phosphorylation of MTOR protein] 		CTD PMID:35130734 NCBI chr 5:164,167,985...164,277,438
Ensembl chr 5:158,884,804...158,994,311 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 affects localization ISO butein affects the localization of NFE2L2 protein CTD PMID:23318726 NCBI chr 3:81,001,529...81,031,165
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 affects localization ISO butein affects the localization of NFKB1 protein CTD PMID:20696233 NCBI chr 2:226,689,745...226,805,897
Ensembl chr 2:224,016,214...224,110,404 		JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 increases activity ISO butein results in increased activity of NR1I2 protein CTD PMID:29933105 NCBI chr11:75,965,717...76,006,733
Ensembl chr11:62,460,213...62,496,658 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO butein results in increased cleavage of PARP1 protein CTD PMID:24931875 NCBI chr13:94,839,484...94,871,295
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Pttg1 PTTG1 regulator of sister chromatid separation, securin decreases expression
decreases response to substance 		ISO butein results in decreased expression of PTTG1 protein
PTTG1 protein results in decreased susceptibility to butein 		CTD PMID:24931875 NCBI chr10:27,893,466...27,904,965
Ensembl chr10:27,893,689...27,904,837 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit affects localization ISO butein affects the localization of RELA protein CTD PMID:20696233 NCBI chr 1:212,354,336...212,364,815
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Sirt1 sirtuin 1 increases activity ISO butein results in increased activity of SIRT1 protein CTD PMID:17327447 NCBI chr20:25,305,953...25,328,000
Ensembl chr20:25,306,917...25,329,260 		JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO butein affects the reaction [IL6 protein affects the phosphorylation of STAT3 protein] CTD PMID:35130734 NCBI chr10:86,311,528...86,363,513
Ensembl chr10:85,811,218...85,863,057 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO 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 chr20:3,626,685...3,629,303
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Vegfa vascular endothelial growth factor A decreases expression ISO butein results in decreased expression of VEGFA mRNA CTD PMID:20696233 NCBI chr 9:22,452,854...22,468,194
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 20856
    role 20816
      chemical role 20394
        antioxidant 16461
          butein 27
Path 2
Term Annotations click to browse term
  CHEBI ontology 20856
    subatomic particle 20854
      composite particle 20854
        hadron 20854
          baryon 20854
            nucleon 20854
              atomic nucleus 20854
                atom 20854
                  main group element atom 20777
                    p-block element atom 20777
                      carbon group element atom 20710
                        carbon atom 20704
                          organic molecular entity 20704
                            heteroorganic entity 20215
                              organochalcogen compound 19902
                                organooxygen compound 19804
                                  carbonyl compound 19435
                                    ketone 17451
                                      alpha,beta-unsaturated ketone 10063
                                        enone 10063
                                          chalcones 947
                                            butein 27
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