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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:4-coumaric acid
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Accession:CHEBI:36090 term browser browse the term
Definition:A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.
Synonyms:exact_synonym: 3-(4-hydroxyphenyl)prop-2-enoic acid
 related_synonym: 3-(4-hydroxyphenyl)-2-propenoic acid;   3-(4-hydroxyphenyl)acrylic acid;   4-hydroxycinnamic acid;   Formula=C9H8O3;   InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12);   InChIKey=NGSWKAQJJWESNS-UHFFFAOYSA-N;   SMILES=[H]C(=Cc1ccc(O)cc1)C(O)=O;   beta-[4-hydroxyphenyl]acrylic acid;   p-coumaric acid;   p-hydroxycinnamic acid;   p-hydroxyphenylacrylic acid;   para-coumaric acid
 alt_id: CHEBI:20348;   CHEBI:20405
 xref: Beilstein:2207381;   CAS:7400-08-0
 xref_mesh: MESH:C032171
 xref: PMID:11684179;   PMID:19089825;   PMID:19930809;   PMID:22447332;   PMID:22585412;   PMID:22923003;   PMID:23178520;   PMID:23420453;   PMID:23485470;   PMID:23669407;   PMID:23684599;   PMID:23810795;   PMID:23857900;   PMID:23892112;   PMID:24927550;   PMID:7285584;   Wikipedia:4-coumaric_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:32373


show annotations for term's descendants           Sort by:
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 bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 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: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 ISO [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 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 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 4:17,317,343...17,410,084
Ensembl chr 4:17,354,466...17,513,903 		JBrowse link
G Erbb2 erb-b2 receptor tyrosine kinase 2 increases response to substance
decreases expression		 ISO ERBB2 protein results in increased susceptibility to bisdemethoxycurcumin
bisdemethoxycurcumin results in decreased expression 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 Gclm glutamate cysteine ligase, modifier subunit increases expression ISO bisdemethoxycurcumin results in increased expression of GCLM mRNA; bisdemethoxycurcumin 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 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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Kdr kinase insert domain receptor multiple interactions ISO [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 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 [bisdemethoxycurcumin 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 bisdemethoxycurcumin 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]; bisdemethoxycurcumin 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 bisdemethoxycurcumin 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]; bisdemethoxycurcumin 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 Mgat3 beta-1,4-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase multiple interactions
increases expression		 ISO [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 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 bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 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 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 bisdemethoxycurcumin 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		 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 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 bisdemethoxycurcumin results in increased expression of NQO1 mRNA; bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 bisdemethoxycurcumin 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 [bisdemethoxycurcumin 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 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 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 bisdemethoxycurcumin 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 Tlr2 toll-like receptor 2 multiple interactions ISO [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 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 [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 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 [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 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 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 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 [bisdemethoxycurcumin 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 Vegfa vascular endothelial growth factor A multiple interactions ISO [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 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 bisdemethoxycurcumin results in decreased expression of WT1 mRNA; bisdemethoxycurcumin 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
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19818
    role 19790
      biological role 19788
        biochemical role 19501
          metabolite 19486
            eukaryotic metabolite 19284
              plant metabolite 17891
                4-coumaric acid 33
                  2-(p-coumaroyl)malic acid 0
                  3-(2-methoxyphenyl)-2-propenoic acid 0
                  3-p-coumaroylquinic acid 0
                  4-O-beta-D-glucosyl-4-coumaric acid + 0
                  4-coumaric acid methyl ester + 0
                  4-coumaroyl-CoA + 0
                  4-p-coumaroylquinic acid + 0
                  5-p-coumaroylquinic acid 0
                  7-O-(6-p-coumaroylglucosyl)chrysoeriol 0
                  bisdemethoxycurcumin 33
                  cadabicine sulfate 0
                  cis-4-coumaric acid + 0
                  p-coumaroylagmatine + 0
                  p-coutaric acid + 0
                  spermidine hydroxycinnamic acid conjugate + 0
                  trans-4-coumaric acid + 0
                  tricoumaroyl spermidine 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19818
    subatomic particle 19816
      composite particle 19816
        hadron 19816
          baryon 19816
            nucleon 19816
              atomic nucleus 19816
                atom 19816
                  main group element atom 19761
                    p-block element atom 19761
                      carbon group element atom 19703
                        carbon atom 19698
                          organic molecular entity 19698
                            organic group 18905
                              organic divalent group 18887
                                organodiyl group 18887
                                  carbonyl group 18853
                                    carbonyl compound 18853
                                      carboxylic acid 18569
                                        monocarboxylic acid 17903
                                          alpha,beta-unsaturated monocarboxylic acid 13205
                                            cinnamic acids 2484
                                              hydroxycinnamic acid 1340
                                                monohydroxycinnamic acid 1000
                                                  coumaric acid 33
                                                    4-coumaric acid 33
                                                      2-(p-coumaroyl)malic acid 0
                                                      3-(2-methoxyphenyl)-2-propenoic acid 0
                                                      3-p-coumaroylquinic acid 0
                                                      4-O-beta-D-glucosyl-4-coumaric acid + 0
                                                      4-coumaric acid methyl ester + 0
                                                      4-coumaroyl-CoA + 0
                                                      4-p-coumaroylquinic acid + 0
                                                      5-p-coumaroylquinic acid 0
                                                      7-O-(6-p-coumaroylglucosyl)chrysoeriol 0
                                                      bisdemethoxycurcumin 33
                                                      cadabicine sulfate 0
                                                      cis-4-coumaric acid + 0
                                                      p-coumaroylagmatine + 0
                                                      p-coutaric acid + 0
                                                      spermidine hydroxycinnamic acid conjugate + 0
                                                      trans-4-coumaric acid + 0
                                                      tricoumaroyl spermidine 0
paths to the root