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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 chr10:549,537...672,235
Ensembl chr10:549,883...672,196
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 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Ache acetylcholinesterase decreases activity EXP demethoxycurcumin results in decreased activity of ACHE protein CTD PMID:18930076 NCBI chr12:22,472,358...22,477,052
Ensembl chr12:22,472,358...22,478,753
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]
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
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 chr11:24,425,013...24,641,872
Ensembl chr11:24,425,005...24,641,858
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 chr13:89,053,457...89,242,531
Ensembl chr13:89,055,983...89,242,443
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 8:2,658,892...2,686,160
Ensembl chr 8:2,659,865...2,686,160
JBrowse link
G Casp3 caspase 3 multiple interactions ISO demethoxycurcumin inhibits the reaction [Peroxynitrous Acid results in increased activity of CASP3 protein] CTD PMID:19188863 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 4:14,150,309...14,191,498
Ensembl chr 4:14,001,761...14,249,749
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 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
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 4:98,648,513...98,709,695
Ensembl chr 4:98,648,545...98,709,694
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 chr10:94,588,555...94,682,072
Ensembl chr10:94,588,555...94,681,914
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 2:225,827,504...225,847,876
Ensembl chr 2:225,827,504...225,847,874
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
increases expression
ISO [demethoxycurcumin co-treated with bis(4-hydroxycinnamoyl)methane] 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 promotes the reaction [malondialdehyde-low density lipoprotein, human results in increased expression of HMOX1 mRNA]
demethoxycurcumin results in increased expression of HMOX1 mRNA; demethoxycurcumin 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 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 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
JBrowse link
G Ins2 insulin 2 increases secretion ISO demethoxycurcumin results in increased secretion of INS protein CTD PMID:19188863 NCBI chr 1:215,856,967...215,858,034
Ensembl chr 1:215,856,971...215,858,034
JBrowse link
G Kdr kinase insert domain receptor affects expression ISO demethoxycurcumin affects the expression of KDR mRNA CTD PMID:17960570 NCBI chr14:34,727,677...34,787,127
Ensembl chr14:34,727,623...34,787,183
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 8:22,250,518...22,259,868
Ensembl chr 8:22,250,518...22,259,779
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO demethoxycurcumin 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 demethoxycurcumin 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 Mmp14 matrix metallopeptidase 14 decreases expression ISO demethoxycurcumin 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 demethoxycurcumin 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 demethoxycurcumin 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 demethoxycurcumin 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 demethoxycurcumin 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 [demethoxycurcumin 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 demethoxycurcumin 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
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 chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression ISO demethoxycurcumin results in increased expression of NQO1 mRNA; demethoxycurcumin 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 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 4:163,239,853...163,261,937
Ensembl chr 4:163,239,849...163,261,958
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 chr10:94,850,971...94,913,202 JBrowse link
G Plau plasminogen activator, urokinase decreases secretion ISO demethoxycurcumin 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 demethoxycurcumin 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 [demethoxycurcumin 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 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 chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Timp2 TIMP metallopeptidase inhibitor 2 decreases expression ISO demethoxycurcumin 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 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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Vegfa vascular endothelial growth factor A affects expression ISO demethoxycurcumin affects the expression of VEGFA mRNA CTD PMID:17960570 NCBI chr 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
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 3:95,133,221...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
      application 19393
        anti-inflammatory agent 14950
          demethoxycurcumin 38
Path 2
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  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
                                      ketone 16144
                                        alpha,beta-unsaturated ketone 8520
                                          enone 8520
                                            demethoxycurcumin 38
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.