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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 decreases activity ISO bis(4-hydroxycinnamoyl)methane results in decreased activity of ABCC1 protein; curcumin III results in decreased activity of ABCC1 protein CTD PMID:15885658, PMID:16021489 NCBI chr10:549,537...672,235
Ensembl chr10:549,883...672,196
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 decreases activity ISO bis(4-hydroxycinnamoyl)methane results in decreased activity of ABCC2 protein CTD PMID:15885658 NCBI chr 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Akt1 AKT serine/threonine kinase 1 increases phosphorylation
multiple interactions
ISO bis(4-hydroxycinnamoyl)methane results in increased phosphorylation of AKT1 protein
AKT1 protein affects the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]
CTD PMID:17535857 NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
JBrowse link
G App amyloid beta precursor protein multiple interactions ISO [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of MGAT3 mRNA; [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of TLR2 mRNA; [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of TLR3 mRNA; [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of TLR4 mRNA; [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of VDR mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of MGAT3 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of TLR2 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of TLR3 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of TLR4 mRNA; bis(4-hydroxycinnamoyl)methane inhibits the reaction [APP protein binds to APP protein] CTD PMID:19715544, PMID:22029407 NCBI chr11:24,425,013...24,641,872
Ensembl chr11:24,425,005...24,641,858
JBrowse link
G Cd36 CD36 molecule increases expression
multiple interactions
ISO bis(4-hydroxycinnamoyl)methane results in increased expression of CD36 mRNA
bis(4-hydroxycinnamoyl)methane inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of CD36 mRNA]
CTD PMID:23386263 NCBI chr 4:14,150,309...14,191,498
Ensembl chr 4:14,001,761...14,249,749
JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit increases expression ISO bis(4-hydroxycinnamoyl)methane results in increased expression of GCLM mRNA; bis(4-hydroxycinnamoyl)methane results in increased expression of GCLM protein CTD PMID:17535857, PMID:19188863 NCBI chr 2:225,827,504...225,847,876
Ensembl chr 2:225,827,504...225,847,874
JBrowse link
G Hmox1 heme oxygenase 1 increases expression
multiple interactions
ISO bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA; bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 protein
[demethoxycurcumin co-treated with bis(4-hydroxycinnamoyl)methane] results in increased expression of HMOX1 mRNA; AKT1 protein affects the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]; KEAP1 protein inhibits the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]; PRKCD protein affects the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]; rottlerin inhibits the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]; rottlerin inhibits the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 protein]; wortmannin inhibits the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]; wortmannin inhibits the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 protein]
CTD PMID:17535857, PMID:19188863, PMID:23386263 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions ISO KEAP1 protein inhibits the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA] CTD PMID:17535857 NCBI chr 8:22,250,518...22,259,868
Ensembl chr 8:22,250,518...22,259,779
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO bis(4-hydroxycinnamoyl)methane results in increased phosphorylation of MAPK1 protein CTD PMID:17535857 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation ISO bis(4-hydroxycinnamoyl)methane results in increased phosphorylation of MAPK3 protein CTD PMID:17535857 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mgat3 beta-1,4-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase multiple interactions
increases expression
ISO [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of MGAT3 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of MGAT3 mRNA
bis(4-hydroxycinnamoyl)methane results in increased expression of MGAT3 mRNA
CTD PMID:19090986, PMID:22029407 NCBI chr 7:121,394,541...121,436,935
Ensembl chr 7:121,408,829...121,435,022
JBrowse link
G Mmp14 matrix metallopeptidase 14 decreases expression ISO bis(4-hydroxycinnamoyl)methane results in decreased expression of MMP14 protein CTD PMID:18495463 NCBI chr15:33,074,441...33,083,666
Ensembl chr15:33,074,441...33,083,655
JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions ISO bis(4-hydroxycinnamoyl)methane results in decreased secretion of and results in decreased activity of MMP2 protein modified form CTD PMID:18495463 NCBI chr19:15,542,771...15,570,589
Ensembl chr19:15,542,765...15,570,611
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO bis(4-hydroxycinnamoyl)methane results in decreased secretion of and results in decreased activity of MMP9 protein CTD PMID:18495463 NCBI chr 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
JBrowse link
G Msr1 macrophage scavenger receptor 1 multiple interactions ISO bis(4-hydroxycinnamoyl)methane inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of MSR1 mRNA] CTD PMID:23386263 NCBI chr16:56,817,714...56,900,025
Ensembl chr16:56,813,791...56,900,052
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 affects localization
multiple interactions
ISO bis(4-hydroxycinnamoyl)methane affects the localization of NFE2L2 protein
[demethoxycurcumin co-treated with bis(4-hydroxycinnamoyl)methane] affects the localization of NFE2L2 protein; NFE2L2 protein affects the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA]
CTD PMID:17535857 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of and results in increased degradation of NFKBIA protein] CTD PMID:18449507 NCBI chr 6:76,267,227...76,270,457
Ensembl chr 6:76,267,228...76,270,457
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO
EXP
bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]; bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:18449507, PMID:18481332, PMID:18838107, PMID:19188055 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression ISO bis(4-hydroxycinnamoyl)methane results in increased expression of NQO1 mRNA; bis(4-hydroxycinnamoyl)methane results in increased expression of NQO1 protein CTD PMID:17535857, PMID:19188863 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Plau plasminogen activator, urokinase decreases secretion ISO bis(4-hydroxycinnamoyl)methane results in decreased secretion of PLAU protein CTD PMID:18495463 NCBI chr15:3,644,296...3,650,765
Ensembl chr15:3,644,769...3,650,819
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma affects binding ISO bis(4-hydroxycinnamoyl)methane binds to PPARG protein CTD PMID:15713005 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Prkcd protein kinase C, delta multiple interactions ISO PRKCD protein affects the reaction [bis(4-hydroxycinnamoyl)methane results in increased expression of HMOX1 mRNA] CTD PMID:17535857 NCBI chr16:6,655,131...6,675,746
Ensembl chr16:6,655,120...6,675,746
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 mRNA]; bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 protein] CTD PMID:18449507 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Timp2 TIMP metallopeptidase inhibitor 2 decreases expression ISO bis(4-hydroxycinnamoyl)methane results in decreased expression of TIMP2 protein CTD PMID:18495463 NCBI chr10:107,338,465...107,386,072
Ensembl chr10:107,338,465...107,386,072
JBrowse link
G Tlr2 toll-like receptor 2 multiple interactions ISO [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of TLR2 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of TLR2 mRNA CTD PMID:22029407 NCBI chr 2:182,840,171...182,846,061
Ensembl chr 2:182,840,727...182,846,061
JBrowse link
G Tlr3 toll-like receptor 3 multiple interactions ISO [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of TLR3 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of TLR3 mRNA CTD PMID:22029407 NCBI chr16:50,016,466...50,031,011
Ensembl chr16:50,016,857...50,031,214
JBrowse link
G Tlr4 toll-like receptor 4 multiple interactions ISO [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of TLR4 mRNA; [bis(4-hydroxycinnamoyl)methane co-treated with APP protein] results in increased expression of TLR4 mRNA CTD PMID:22029407 NCBI chr 5:82,587,424...82,601,056
Ensembl chr 5:82,587,420...82,601,052
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]; bis(4-hydroxycinnamoyl)methane inhibits the reaction [Lipopolysaccharides results in increased expression of TNF protein] CTD PMID:18838107 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Vdr vitamin D receptor multiple interactions ISO [bis(4-hydroxycinnamoyl)methane analog co-treated with APP protein] results in increased expression of VDR mRNA CTD PMID:22029407 NCBI chr 7:139,344,452...139,394,138
Ensembl chr 7:139,342,063...139,394,166
JBrowse link
G Wt1 WT1 transcription factor decreases expression ISO bis(4-hydroxycinnamoyl)methane results in decreased expression of WT1 mRNA; bis(4-hydroxycinnamoyl)methane results in decreased expression of WT1 protein CTD PMID:18034345 NCBI chr 3:95,133,221...95,180,574
Ensembl chr 3:95,133,713...95,180,564
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      biological role 19734
        biochemical role 19282
          metabolite 19263
            bisdemethoxycurcumin 30
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    p-block element atom 19672
                      carbon group element atom 19574
                        carbon atom 19563
                          organic molecular entity 19563
                            organic group 18495
                              organic divalent group 18488
                                organodiyl group 18488
                                  carbonyl group 18391
                                    carbonyl compound 18391
                                      carboxylic acid 18061
                                        monocarboxylic acid 17407
                                          alpha,beta-unsaturated monocarboxylic acid 11359
                                            cinnamic acids 2375
                                              hydroxycinnamic acid 1252
                                                monohydroxycinnamic acid 917
                                                  coumaric acid 30
                                                    4-coumaric acid 30
                                                      bisdemethoxycurcumin 30
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.