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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:demethoxycurcumin
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Accession:CHEBI:65737 term browser browse the term
Definition:A beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior.
Synonyms:related_synonym: (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;   (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione;   4-hydroxycinnamoyl(feroyl)methane;   4-hydroxycinnamoyl(feruloyl)methane;   BHCFM;   Formula=C20H18O5;   InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+;   InChIKey=HJTVQHVGMGKONQ-LUZURFALSA-N;   SMILES=COc1cc(\\C=C\\C(=O)CC(=O)\\C=C\\c2ccc(O)cc2)ccc1O;   curcuminII;   feruloyl-p-hydroxycinnnamoylmethane
 xref: CAS:22608-11-3;   CAS:24939-17-1;   KEGG:C17742
 xref_mesh: MESH:C050229
 xref: MetaCyc:CPD-12187;   PMID:12059141;   PMID:15730265;   PMID:17553917;   PMID:18449507;   PMID:18826228;   PMID:19818349;   PMID:22454662;   PMID:22552297;   Reaxys:5589254



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demethoxycurcumin 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 demethoxycurcumin 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 demethoxycurcumin 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 Ache acetylcholinesterase decreases activity EXP demethoxycurcumin results in decreased activity of ACHE protein CTD PMID:18930076 NCBI chr12:19,406,133...19,413,713
Ensembl chr12:19,407,360...19,413,651
JBrowse link
G Akt1 AKT serine/threonine kinase 1 increases phosphorylation
multiple interactions
ISO demethoxycurcumin results in increased phosphorylation of AKT1 protein
AKT1 protein affects the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]
[bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]
CTD PMID:17535857 PMID:35752269 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
decreases secretion
ISO demethoxycurcumin inhibits the reaction [APP protein binds to APP protein]
demethoxycurcumin results in decreased secretion of APP protein
CTD PMID:19715544 NCBI chr11:24,019,774...24,236,584
Ensembl chr11:24,019,778...24,236,561
JBrowse link
G Atf6 activating transcription factor 6 multiple interactions ISO demethoxycurcumin analog inhibits the reaction [Thapsigargin results in increased expression of ATF6 protein] CTD PMID:26264395 NCBI chr13:82,927,579...83,106,381
Ensembl chr13:82,930,034...83,107,177
JBrowse link
G Bak1 BCL2-antagonist/killer 1 decreases expression ISO demethoxycurcumin results in decreased expression of BAK1 mRNA CTD PMID:33582110 NCBI chr20:5,100,480...5,109,669
Ensembl chr20:5,100,480...5,109,264
JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO demethoxycurcumin results in increased expression of BAX protein CTD PMID:34291863 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO demethoxycurcumin results in decreased expression of BCL2 protein CTD PMID:34291863 NCBI chr13:22,689,783...22,853,920
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 demethoxycurcumin results in decreased expression of BCL2L1 mRNA; demethoxycurcumin results in decreased expression of BCL2L1 protein CTD PMID:33582110 PMID:34291863 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479
JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 decreases expression ISO demethoxycurcumin results in decreased expression of BIRC5 protein CTD PMID:34291863 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380
JBrowse link
G Casp12 caspase 12 multiple interactions ISO demethoxycurcumin analog inhibits the reaction [Thapsigargin results in increased expression of CASP12 protein modified form] CTD PMID:26264395 NCBI chr 8:2,642,296...2,669,549
Ensembl chr 8:2,642,434...2,674,037
JBrowse link
G Casp3 caspase 3 multiple interactions
decreases expression
increases cleavage
ISO demethoxycurcumin inhibits the reaction [Peroxynitrous Acid results in increased activity of CASP3 protein]
demethoxycurcumin results in decreased expression of CASP3 mRNA
demethoxycurcumin results in increased cleavage of CASP3 protein
CTD PMID:19188863 PMID:33582110 PMID:34291863 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 decreases expression ISO demethoxycurcumin results in decreased expression of CASP8 mRNA CTD PMID:33582110 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 increases activity
decreases expression
increases cleavage
ISO demethoxycurcumin results in increased activity of CASP9 protein
demethoxycurcumin results in decreased expression of CASP9 mRNA
demethoxycurcumin results in increased cleavage of CASP9 protein
CTD PMID:33582110 PMID:34291863 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Cd36 CD36 molecule multiple interactions ISO demethoxycurcumin inhibits the reaction [malondialdehyde-low density lipoprotein, human results in increased expression of CD36 mRNA]; demethoxycurcumin inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of CD36 mRNA]; demethoxycurcumin inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of CD36 protein] CTD PMID:23386263 NCBI chr 4:17,317,343...17,410,084
Ensembl chr 4:17,354,466...17,513,903
JBrowse link
G Cdk4 cyclin-dependent kinase 4 decreases expression ISO demethoxycurcumin results in decreased expression of CDK4 protein CTD PMID:34291863 NCBI chr 7:62,886,124...62,889,562
Ensembl chr 7:62,883,105...62,942,403
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO demethoxycurcumin results in increased expression of CDKN1A mRNA CTD PMID:33582110 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions ISO demethoxycurcumin analog inhibits the reaction [Thapsigargin results in increased expression of DDIT3 protein] CTD PMID:26264395 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Eif2ak3 eukaryotic translation initiation factor 2 alpha kinase 3 multiple interactions ISO demethoxycurcumin analog inhibits the reaction [Thapsigargin results in increased phosphorylation of EIF2AK3 protein] CTD PMID:26264395 NCBI chr 4:102,805,495...102,866,914
Ensembl chr 4:102,805,510...102,866,911
JBrowse link
G Erbb2 erb-b2 receptor tyrosine kinase 2 increases response to substance
multiple interactions
ISO ERBB2 protein results in increased susceptibility to demethoxycurcumin
benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [demethoxycurcumin results in increased degradation of ERBB2 protein]; demethoxycurcumin results in decreased expression of and results in increased degradation of ERBB2 protein
CTD PMID:34291863 NCBI chr10:83,411,197...83,435,078
Ensembl chr10:83,411,313...83,435,078
JBrowse link
G Ern1 endoplasmic reticulum to nucleus signaling 1 multiple interactions ISO demethoxycurcumin analog inhibits the reaction [Thapsigargin results in increased phosphorylation of ERN1 protein] CTD PMID:26264395 NCBI chr10:91,326,889...91,421,201
Ensembl chr10:91,330,654...91,421,029
JBrowse link
G Gadd45a growth arrest and DNA-damage-inducible, alpha increases expression ISO demethoxycurcumin results in increased expression of GADD45A mRNA CTD PMID:33582110 NCBI chr 4:96,154,789...96,157,091
Ensembl chr 4:96,154,789...96,157,115
JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit increases expression ISO demethoxycurcumin results in increased expression of GCLM mRNA
demethoxycurcumin results in increased expression of GCLM mRNA; demethoxycurcumin results in increased expression of GCLM protein
CTD PMID:17535857 PMID:19188863 PMID:23386263 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 multiple interactions
increases expression
ISO [demethoxycurcumin co-treated with bisdemethoxycurcumin] results in increased expression of HMOX1 mRNA; AKT1 protein affects the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]; KEAP1 protein inhibits the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]; NFE2L2 protein affects the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]; PRKCD protein affects the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]; rottlerin inhibits the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]; rottlerin inhibits the reaction [demethoxycurcumin results in increased expression of HMOX1 protein]; Wortmannin inhibits the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]; Wortmannin inhibits the reaction [demethoxycurcumin results in increased expression of HMOX1 protein]
demethoxycurcumin results in increased expression of HMOX1 mRNA; demethoxycurcumin results in increased expression of HMOX1 protein
demethoxycurcumin promotes the reaction [malondialdehyde-low density lipoprotein, human results in increased expression of HMOX1 mRNA]
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 Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions ISO demethoxycurcumin analog inhibits the reaction [Thapsigargin results in increased expression of HSPA5 protein] CTD PMID:26264395 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891
JBrowse link
G Ins2 insulin 2 increases secretion ISO demethoxycurcumin results in increased secretion of INS protein CTD PMID:19188863 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775
JBrowse link
G Kdr kinase insert domain receptor affects expression
multiple interactions
ISO demethoxycurcumin affects the expression of KDR mRNA
[bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein]
CTD PMID:17960570 PMID:35752269 NCBI chr14:32,217,871...32,261,018
Ensembl chr14:32,217,871...32,261,018
JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions ISO KEAP1 protein inhibits the reaction [demethoxycurcumin 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
multiple interactions
ISO demethoxycurcumin 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 MAPK1 protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK1 protein]
CTD PMID:17535857 PMID:35752269 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
multiple interactions
ISO demethoxycurcumin results in increased phosphorylation of MAPK3 protein
[bisdemethoxycurcumin co-treated with Curcumin co-treated with demethoxycurcumin] inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein]
CTD PMID:17535857 PMID:35752269 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mmp14 matrix metallopeptidase 14 decreases expression ISO demethoxycurcumin 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 demethoxycurcumin 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 demethoxycurcumin 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 demethoxycurcumin inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of MSR1 mRNA] CTD PMID:23386263 NCBI chr16:52,717,775...52,803,602
Ensembl chr16:52,717,732...52,799,676
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 affects localization
multiple interactions
ISO demethoxycurcumin affects the localization of NFE2L2 protein
[demethoxycurcumin co-treated with bisdemethoxycurcumin] affects the localization of NFE2L2 protein; NFE2L2 protein affects the reaction [demethoxycurcumin results in increased expression of HMOX1 mRNA]
CTD PMID:17535857 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO demethoxycurcumin 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
demethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]; demethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:18449507 PMID:18838107 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 demethoxycurcumin results in increased expression of NQO1 mRNA; demethoxycurcumin 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 Olr1 oxidized low density lipoprotein receptor 1 multiple interactions ISO demethoxycurcumin inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of OLR1 mRNA] CTD PMID:23386263 NCBI chr 4:162,926,436...162,949,057
Ensembl chr 4:162,926,439...162,948,523
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
multiple interactions
ISO demethoxycurcumin results in increased cleavage of PARP1 protein
Wortmannin promotes the reaction [demethoxycurcumin results in increased cleavage of PARP1 protein]
CTD PMID:34291863 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Pecam1 platelet and endothelial cell adhesion molecule 1 increases expression EXP demethoxycurcumin results in increased expression of PECAM1 protein CTD PMID:17960570 NCBI chr10:91,590,521...91,652,279
Ensembl chr10:91,590,521...91,652,116
JBrowse link
G Plau plasminogen activator, urokinase decreases secretion ISO demethoxycurcumin 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 demethoxycurcumin 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 [demethoxycurcumin results in increased expression of HMOX1 mRNA] CTD PMID:17535857 NCBI chr16:5,769,217...5,799,380
Ensembl chr16:5,769,215...5,799,352
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO demethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 mRNA]; demethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 protein] CTD PMID:18449507 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Raf1 Raf-1 proto-oncogene, serine/threonine kinase decreases expression ISO demethoxycurcumin results in decreased expression of RAF1 protein CTD PMID:34291863 NCBI chr 4:148,679,534...148,740,265
Ensembl chr 4:148,679,530...148,740,317
JBrowse link
G Timp2 TIMP metallopeptidase inhibitor 2 decreases expression ISO demethoxycurcumin results in decreased expression of TIMP2 protein CTD PMID:18495463 NCBI chr10:103,541,199...103,590,611
Ensembl chr10:103,531,505...103,590,611
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP demethoxycurcumin inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]; demethoxycurcumin 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 Vegfa vascular endothelial growth factor A affects expression
multiple interactions
ISO demethoxycurcumin affects the expression of VEGFA mRNA
[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]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of KDR protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK1 protein]; demethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of MAPK3 protein]
CTD PMID:17960570 PMID:35752269 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
JBrowse link
G Wt1 WT1 transcription factor decreases expression ISO demethoxycurcumin results in decreased expression of WT1 mRNA; demethoxycurcumin 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
G Xiap X-linked inhibitor of apoptosis decreases expression ISO demethoxycurcumin results in decreased expression of XIAP protein CTD PMID:34291863 NCBI chr  X:120,890,537...120,938,413
Ensembl chr  X:120,897,907...120,934,700
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19918
    role 19894
      application 19729
        anti-inflammatory agent 16531
          demethoxycurcumin 52
Path 2
Term Annotations click to browse term
  CHEBI ontology 19918
    subatomic particle 19916
      composite particle 19916
        hadron 19916
          baryon 19916
            nucleon 19916
              atomic nucleus 19916
                atom 19916
                  main group element atom 19866
                    p-block element atom 19866
                      carbon group element atom 19811
                        carbon atom 19806
                          organic molecular entity 19806
                            organic group 18995
                              organic divalent group 18969
                                organodiyl group 18969
                                  carbonyl group 18922
                                    carbonyl compound 18922
                                      ketone 17210
                                        alpha,beta-unsaturated ketone 9978
                                          enone 9978
                                            demethoxycurcumin 52
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