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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:bisdemethoxycurcumin
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Accession:CHEBI:71045 term browser browse the term
Definition:A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.
Synonyms:exact_synonym: (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
 related_synonym: 1,7-Bis(4-hydroxyphenyl)-1,6-Heptadiene-3,5-dione;   Bis(4-hydroxycinnamoyl)methane;   Bis(p-hydroxycinnamoyl)methane;   Curcumin III;   Didemethoxycurcumin;   Formula=C19H16O4;   InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+;   InChIKey=PREBVFJICNPEKM-YDWXAUTNSA-N;   SMILES=Oc1ccc(cc1)\\C=C\\C(=O)CC(=O)\\C=C\\c1ccc(O)cc1
 xref: CAS:24939-16-0;   CAS:33171-05-0;   KEGG:C17743
 xref_mesh: MESH:C034786
 xref: MetaCyc:CPD-12188;   PMID:20953820;   PMID:21041675;   PMID:21136025;   PMID:21484077;   PMID:21640982;   PMID:21856253;   PMID:21933103;   PMID:21941764;   PMID:21968952;   PMID:22029407;   PMID:22145830;   PMID:22156608;   PMID:22207005;   PMID:22237476;   PMID:22434443;   PMID:22457548;   PMID:22531131;   PMID:22566109;   PMID:22725836;   PMID:22753036;   PMID:22768090;   PMID:22849866;   PMID:22928089;   PMID:22980852;   PMID:23079892;   Patent:US2006258752;   Patent:US2010048957;   Patent:WO2007011674;   Reaxys:3149384


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bisdemethoxycurcumin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G ABCC1 ATP binding cassette subfamily C member 1 (ABCC1 blood group) decreases activity EXP bisdemethoxycurcumin results in decreased activity of ABCC1 protein; curcumin III results in decreased activity of ABCC1 protein CTD PMID:15885658 PMID:16021489 NCBI chr16:15,949,143...16,143,053
Ensembl chr16:15,949,138...16,143,257 		JBrowse link
G ABCC2 ATP binding cassette subfamily C member 2 decreases activity EXP bisdemethoxycurcumin results in decreased activity of ABCC2 protein CTD PMID:15885658 NCBI chr10:99,782,640...99,852,594
Ensembl chr10:99,782,640...99,852,594 		JBrowse link
G AKT1 AKT serine/threonine kinase 1 increases phosphorylation
decreases expression
multiple interactions		 ISO
EXP		 bisdemethoxycurcumin results in increased phosphorylation of AKT1 protein
bisdemethoxycurcumin results in decreased expression of AKT1 protein modified form
[bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]
AKT1 protein affects the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]		 CTD PMID:17535857 PMID:35735092 PMID:35752269 NCBI chr14:104,769,349...104,795,748
Ensembl chr14:104,769,349...104,795,751 		JBrowse link
G APP amyloid beta precursor protein multiple interactions EXP [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of MGAT3 mRNA; [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of TLR2 mRNA; [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of TLR3 mRNA; [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of TLR4 mRNA; [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of VDR mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of MGAT3 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of TLR2 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of TLR3 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of TLR4 mRNA; bisdemethoxycurcumin inhibits the reaction [APP protein binds to APP protein] CTD PMID:19715544 PMID:22029407 NCBI chr21:25,880,550...26,171,128
Ensembl chr21:25,880,535...26,171,128 		JBrowse link
G CD36 CD36 molecule (CD36 blood group) increases expression
multiple interactions		 EXP bisdemethoxycurcumin results in increased expression of CD36 mRNA
bisdemethoxycurcumin inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of CD36 mRNA]		 CTD PMID:23386263 NCBI chr 7:80,602,207...80,679,274
Ensembl chr 7:80,369,575...80,679,277 		JBrowse link
G EGFR epidermal growth factor receptor decreases expression EXP bisdemethoxycurcumin results in decreased expression of EGFR protein modified form CTD PMID:35735092 NCBI chr 7:55,019,017...55,211,628
Ensembl chr 7:55,019,017...55,211,628 		JBrowse link
G ERBB2 erb-b2 receptor tyrosine kinase 2 increases response to substance
decreases expression		 EXP ERBB2 protein results in increased susceptibility to bisdemethoxycurcumin
bisdemethoxycurcumin results in decreased expression of ERBB2 protein		 CTD PMID:34291863 NCBI chr17:39,688,094...39,728,658
Ensembl chr17:39,687,914...39,730,426 		JBrowse link
G GCLM glutamate-cysteine ligase modifier subunit increases expression EXP
ISO		 bisdemethoxycurcumin results in increased expression of GCLM mRNA; bisdemethoxycurcumin results in increased expression of GCLM protein CTD PMID:17535857 PMID:19188863 NCBI chr 1:93,885,199...93,909,430
Ensembl chr 1:93,885,199...93,909,456 		JBrowse link
G GRB2 growth factor receptor bound protein 2 decreases expression EXP bisdemethoxycurcumin results in decreased expression of GRB2 protein CTD PMID:35735092 NCBI chr17:75,318,076...75,405,678
Ensembl chr17:75,318,076...75,405,709 		JBrowse link
G HMOX1 heme oxygenase 1 increases expression
multiple interactions		 ISO
EXP		 bisdemethoxycurcumin results in increased expression of HMOX1 mRNA; bisdemethoxycurcumin results in increased expression of HMOX1 protein
[demethoxycurcumin co-treated with bisdemethoxycurcumin] results in increased expression of HMOX1 mRNA; AKT1 protein affects the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]; KEAP1 protein inhibits the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]; PRKCD protein affects the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]; rottlerin inhibits the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]; rottlerin inhibits the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 protein]; Wortmannin inhibits the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]; Wortmannin inhibits the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 protein]		 CTD PMID:17535857 PMID:19188863 PMID:23386263 NCBI chr22:35,381,096...35,394,207
Ensembl chr22:35,380,361...35,394,214 		JBrowse link
G KDR kinase insert domain receptor multiple interactions EXP [bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein] CTD PMID:35752269 NCBI chr 4:55,078,481...55,125,595
Ensembl chr 4:55,078,481...55,125,595 		JBrowse link
G KEAP1 kelch like ECH associated protein 1 multiple interactions ISO KEAP1 protein inhibits the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA] CTD PMID:17535857 NCBI chr19:10,486,125...10,503,356
Ensembl chr19:10,486,125...10,503,558 		JBrowse link
G MAPK1 mitogen-activated protein kinase 1 increases phosphorylation
decreases expression
multiple interactions		 ISO
EXP		 bisdemethoxycurcumin results in increased phosphorylation of MAPK1 protein
bisdemethoxycurcumin results in decreased expression of MAPK1 protein modified form
[bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK1 protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK1 protein]		 CTD PMID:17535857 PMID:35735092 PMID:35752269 NCBI chr22:21,759,657...21,867,680
Ensembl chr22:21,759,657...21,867,680 		JBrowse link
G MAPK3 mitogen-activated protein kinase 3 increases phosphorylation
decreases expression
multiple interactions		 ISO
EXP		 bisdemethoxycurcumin results in increased phosphorylation of MAPK3 protein
bisdemethoxycurcumin results in decreased expression of MAPK3 protein modified form
[bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein]		 CTD PMID:17535857 PMID:35735092 PMID:35752269 NCBI chr16:30,114,105...30,123,220
Ensembl chr16:30,114,105...30,123,506 		JBrowse link
G MGAT3 beta-1,4-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase multiple interactions
increases expression		 EXP [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of MGAT3 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of MGAT3 mRNA
bisdemethoxycurcumin results in increased expression of MGAT3 mRNA		 CTD PMID:19090986 PMID:22029407 NCBI chr22:39,457,012...39,492,194
Ensembl chr22:39,457,012...39,492,194 		JBrowse link
G MMP14 matrix metallopeptidase 14 decreases expression EXP bisdemethoxycurcumin results in decreased expression of MMP14 protein CTD PMID:18495463 NCBI chr14:22,836,585...22,847,758
Ensembl chr14:22,836,560...22,849,041 		JBrowse link
G MMP2 matrix metallopeptidase 2 multiple interactions
decreases expression		 EXP bisdemethoxycurcumin results in decreased secretion of and results in decreased activity of MMP2 protein modified form
bisdemethoxycurcumin results in decreased expression of MMP2 protein		 CTD PMID:18495463 PMID:35735092 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 bisdemethoxycurcumin results in decreased secretion of and results in decreased activity of MMP9 protein
bisdemethoxycurcumin results in decreased expression of MMP9 protein		 CTD PMID:18495463 PMID:35735092 NCBI chr20:46,008,908...46,016,561
Ensembl chr20:46,008,908...46,016,561 		JBrowse link
G MSR1 macrophage scavenger receptor 1 multiple interactions EXP bisdemethoxycurcumin inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of MSR1 mRNA] CTD PMID:23386263 NCBI chr 8:16,107,881...16,192,651
Ensembl chr 8:16,107,878...16,567,490 		JBrowse link
G NFE2L2 NFE2 like bZIP transcription factor 2 affects localization
multiple interactions		 ISO bisdemethoxycurcumin affects the localization of NFE2L2 protein
[demethoxycurcumin co-treated with bisdemethoxycurcumin] affects the localization of NFE2L2 protein; NFE2L2 protein affects the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA]		 CTD PMID:17535857 NCBI chr 2:177,230,303...177,264,727
Ensembl chr 2:177,218,667...177,392,756 		JBrowse link
G NFKBIA NFKB inhibitor alpha multiple interactions ISO bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of and results in increased degradation of NFKBIA protein] CTD PMID:18449507 NCBI chr14:35,401,513...35,404,749
Ensembl chr14:35,401,079...35,404,749 		JBrowse link
G NOS2 nitric oxide synthase 2 multiple interactions ISO bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]; bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:18449507 PMID:18481332 PMID:18838107 PMID:19188055 NCBI chr17:27,756,766...27,800,529
Ensembl chr17:27,756,766...27,800,529 		JBrowse link
G NQO1 NAD(P)H quinone dehydrogenase 1 increases expression EXP
ISO		 bisdemethoxycurcumin results in increased expression of NQO1 mRNA; bisdemethoxycurcumin results in increased expression of NQO1 protein CTD PMID:17535857 PMID:19188863 NCBI chr16:69,709,401...69,726,560
Ensembl chr16:69,706,996...69,726,668 		JBrowse link
G PDPK1 3-phosphoinositide dependent protein kinase 1 decreases expression EXP bisdemethoxycurcumin results in decreased expression of PDPK1 protein modified form CTD PMID:35735092 NCBI chr16:2,538,021...2,603,188
Ensembl chr16:2,537,979...2,603,188 		JBrowse link
G PLAU plasminogen activator, urokinase decreases secretion EXP bisdemethoxycurcumin results in decreased secretion of PLAU protein CTD PMID:18495463 NCBI chr10:73,909,164...73,917,494
Ensembl chr10:73,909,177...73,917,496 		JBrowse link
G PPARG peroxisome proliferator activated receptor gamma affects binding EXP bisdemethoxycurcumin binds to PPARG protein CTD PMID:15713005 NCBI chr 3:12,287,368...12,434,344
Ensembl chr 3:12,287,368...12,434,356 		JBrowse link
G PRKCD protein kinase C delta multiple interactions ISO PRKCD protein affects the reaction [bisdemethoxycurcumin results in increased expression of HMOX1 mRNA] CTD PMID:17535857 NCBI chr 3:53,161,209...53,192,717
Ensembl chr 3:53,156,009...53,192,717 		JBrowse link
G PTGS2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 mRNA]; bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 protein] CTD PMID:18449507 NCBI chr 1:186,671,791...186,680,423
Ensembl chr 1:186,671,791...186,680,922 		JBrowse link
G RAF1 Raf-1 proto-oncogene, serine/threonine kinase decreases expression EXP bisdemethoxycurcumin results in decreased expression of RAF1 protein modified form CTD PMID:35735092 NCBI chr 3:12,583,601...12,664,117
Ensembl chr 3:12,582,101...12,664,201 		JBrowse link
G SOS1 SOS Ras/Rac guanine nucleotide exchange factor 1 decreases expression EXP bisdemethoxycurcumin results in decreased expression of SOS1 protein CTD PMID:35735092 NCBI chr 2:38,981,549...39,124,868
Ensembl chr 2:38,962,206...39,124,345 		JBrowse link
G TIMP1 TIMP metallopeptidase inhibitor 1 decreases expression EXP bisdemethoxycurcumin results in decreased expression of TIMP1 protein CTD PMID:35735092 NCBI chr  X:47,582,436...47,586,789
Ensembl chr  X:47,582,408...47,586,789 		JBrowse link
G TIMP2 TIMP metallopeptidase inhibitor 2 decreases expression EXP bisdemethoxycurcumin results in decreased expression of TIMP2 protein CTD PMID:18495463 NCBI chr17:78,852,977...78,925,387
Ensembl chr17:78,852,977...78,925,387 		JBrowse link
G TLR2 toll like receptor 2 multiple interactions EXP [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of TLR2 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of TLR2 mRNA CTD PMID:22029407 NCBI chr 4:153,684,280...153,710,637
Ensembl chr 4:153,684,070...153,706,260 		JBrowse link
G TLR3 toll like receptor 3 multiple interactions EXP [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of TLR3 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of TLR3 mRNA CTD PMID:22029407 NCBI chr 4:186,069,156...186,088,073
Ensembl chr 4:186,068,911...186,088,073 		JBrowse link
G TLR4 toll like receptor 4 multiple interactions EXP [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of TLR4 mRNA; [bisdemethoxycurcumin co-treated with APP protein] results in increased expression of TLR4 mRNA CTD PMID:22029407 NCBI chr 9:117,704,403...117,724,735
Ensembl chr 9:117,704,175...117,724,735 		JBrowse link
G TNF tumor necrosis factor multiple interactions ISO bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]; bisdemethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of TNF protein] CTD PMID:18838107 NCBI chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336 		JBrowse link
G VDR vitamin D receptor multiple interactions EXP [bisdemethoxycurcumin analog co-treated with APP protein] results in increased expression of VDR mRNA CTD PMID:22029407 NCBI chr12:47,841,537...47,904,994
Ensembl chr12:47,841,537...47,943,048 		JBrowse link
G VEGFA vascular endothelial growth factor A multiple interactions EXP [bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]; [bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein]; [bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK1 protein]; [bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK1 protein]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein] CTD PMID:35752269 NCBI chr 6:43,770,211...43,786,487
Ensembl chr 6:43,770,184...43,786,487 		JBrowse link
G WT1 WT1 transcription factor decreases expression EXP bisdemethoxycurcumin results in decreased expression of WT1 mRNA; bisdemethoxycurcumin results in decreased expression of WT1 protein CTD PMID:18034345 NCBI chr11:32,387,775...32,435,539
Ensembl chr11:32,387,775...32,435,564 		JBrowse link
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Term Annotations click to browse term
  CHEBI ontology 26041
    role 25957
      biological role 25936
        biochemical role 25170
          metabolite 25100
            bisdemethoxycurcumin 39
Path 2
Term Annotations click to browse term
  CHEBI ontology 26041
    subatomic particle 26016
      composite particle 26016
        hadron 26016
          baryon 26016
            nucleon 26016
              atomic nucleus 26016
                atom 26016
                  main group element atom 25841
                    p-block element atom 25841
                      carbon group element atom 25441
                        carbon atom 25399
                          organic molecular entity 25399
                            heteroorganic entity 24773
                              organochalcogen compound 24384
                                organooxygen compound 24061
                                  carbon oxoacid 22757
                                    carboxylic acid 22737
                                      monocarboxylic acid 21735
                                        alpha,beta-unsaturated monocarboxylic acid 14332
                                          cinnamic acids 2592
                                            hydroxycinnamic acid 1378
                                              monohydroxycinnamic acid 1037
                                                coumaric acid 39
                                                  4-coumaric acid 39
                                                    bisdemethoxycurcumin 39
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