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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 chr10:528,961...655,179
Ensembl chr10:531,812...655,114
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 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238
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 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
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 chr11:24,019,774...24,236,584
Ensembl chr11:24,019,778...24,236,561
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 4:17,317,343...17,410,084 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 2:210,347,482...210,367,537
Ensembl chr 2:210,347,482...210,367,535
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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
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 8:19,768,375...19,777,862
Ensembl chr 8:19,768,375...19,777,862
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 chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
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 7:111,708,353...111,761,825
Ensembl chr 7:111,675,730...111,762,026
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 chr15:27,887,795...27,897,020
Ensembl chr15:27,887,727...27,899,864
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 chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870
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 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
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 chr16:52,717,775...52,802,890
Ensembl chr16:52,717,732...52,799,676
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 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
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 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
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 chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 chr15:3,456,230...3,462,732
Ensembl chr15:3,456,232...3,462,775
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 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
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 chr16:5,769,226...5,807,214
Ensembl chr16:5,769,215...5,799,352
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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
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 chr10:103,541,199...103,590,611 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 2:169,200,620...169,206,819
Ensembl chr 2:169,197,419...169,206,630
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 chr16:46,821,980...46,837,900
Ensembl chr16:46,822,039...46,836,545
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 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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 7:128,987,981...129,037,677
Ensembl chr 7:128,987,981...129,037,677
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 3:91,566,540...91,613,653
Ensembl chr 3:91,567,001...91,613,643
JBrowse link

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  CHEBI ontology 19812
    role 19761
      biological role 19761
        biochemical role 19381
          metabolite 19356
            bisdemethoxycurcumin 30
Path 2
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  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19708
                    p-block element atom 19708
                      carbon group element atom 19630
                        carbon atom 19620
                          organic molecular entity 19620
                            organic group 18728
                              organic divalent group 18719
                                organodiyl group 18719
                                  carbonyl group 18667
                                    carbonyl compound 18667
                                      carboxylic acid 18364
                                        monocarboxylic acid 17632
                                          alpha,beta-unsaturated monocarboxylic acid 12218
                                            cinnamic acids 2420
                                              hydroxycinnamic acid 1270
                                                monohydroxycinnamic acid 933
                                                  coumaric acid 30
                                                    4-coumaric acid 30
                                                      bisdemethoxycurcumin 30
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