Send us a Message



Submit Data |  Help |  Video Tutorials |  News |  Publications |  Download |  REST API |  Citing RGD |  Contact   

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
go back to main search page
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
decreases expression
ISO bisdemethoxycurcumin results in increased phosphorylation of AKT1 protein
AKT1 protein affects the reaction [bisdemethoxycurcumin 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]; bisdemethoxycurcumin inhibits the reaction [VEGF protein results in increased phosphorylation of AKT1 protein]
bisdemethoxycurcumin results in decreased expression of AKT1 protein modified form
CTD PMID:17535857 PMID:35735092 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 Egfr epidermal growth factor receptor decreases expression ISO bisdemethoxycurcumin results in decreased expression of EGFR protein modified form CTD PMID:35735092 NCBI chr14:91,176,979...91,349,722
Ensembl chr14:91,177,067...91,344,382
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 Grb2 growth factor receptor bound protein 2 decreases expression ISO bisdemethoxycurcumin results in decreased expression of GRB2 protein CTD PMID:35735092 NCBI chr10:100,881,404...100,949,193
Ensembl chr10:100,869,718...100,949,309
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
decreases expression
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]
bisdemethoxycurcumin results in decreased expression of MAPK1 protein modified form
CTD PMID:17535857 PMID:35735092 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
decreases expression
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]
bisdemethoxycurcumin results in decreased expression of MAPK3 protein modified form
CTD PMID:17535857 PMID:35735092 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
decreases expression
ISO bisdemethoxycurcumin results in decreased secretion of and results in decreased activity of MMP2 protein modified form
bisdemethoxycurcumin results in decreased expression of MMP2 protein
CTD PMID:18495463 PMID:35735092 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
decreases expression
ISO bisdemethoxycurcumin results in decreased secretion of and results in decreased activity of MMP9 protein
bisdemethoxycurcumin results in decreased expression of MMP9 protein
CTD PMID:18495463 PMID:35735092 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...52,803,602
Ensembl chr16:52,717,732...52,799,676
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 affects localization
multiple interactions
ISO 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...60,621,712
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 Pdpk1 3-phosphoinositide dependent protein kinase-1 decreases expression ISO bisdemethoxycurcumin results in decreased expression of PDPK1 protein modified form CTD PMID:35735092 NCBI chr10:13,105,435...13,182,664
Ensembl chr10:13,105,498...13,174,623
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 chr16:5,769,217...5,799,380
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 chr13:62,163,936...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 bisdemethoxycurcumin results in decreased expression of RAF1 protein modified form CTD PMID:35735092 NCBI chr 4:148,679,534...148,740,265
Ensembl chr 4:148,679,530...148,740,317
JBrowse link
G Sos1 SOS Ras/Rac guanine nucleotide exchange factor 1 decreases expression ISO bisdemethoxycurcumin results in decreased expression of SOS1 protein CTD PMID:35735092 NCBI chr 6:14,533,870...14,613,348
Ensembl chr 6:14,533,360...14,611,107
JBrowse link
G Timp1 TIMP metallopeptidase inhibitor 1 decreases expression ISO bisdemethoxycurcumin results in decreased expression of TIMP1 protein CTD PMID:35735092 NCBI chr  X:1,212,969...1,217,714
Ensembl chr  X:1,212,972...1,217,664
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 19803
    role 19779
      biological role 19806
        biochemical role 19514
          metabolite 19501
            eukaryotic metabolite 19320
              plant metabolite 17956
                4-coumaric acid 39
                  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
                  Pestalotiopisorin A 0
                  bisdemethoxycurcumin 39
                  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 19803
    subatomic particle 19801
      composite particle 19801
        hadron 19830
          baryon 19830
            nucleon 19830
              atomic nucleus 19830
                atom 19801
                  main group element atom 19780
                    p-block element atom 19780
                      carbon group element atom 19728
                        carbon atom 19725
                          organic molecular entity 19725
                            heteroorganic entity 19479
                              organochalcogen compound 19214
                                organooxygen compound 19129
                                  carbon oxoacid 18617
                                    carboxylic acid 18578
                                      monocarboxylic acid 17966
                                        alpha,beta-unsaturated monocarboxylic acid 13453
                                          cinnamic acids 2508
                                            hydroxycinnamic acid 1362
                                              monohydroxycinnamic acid 1017
                                                coumaric acid 39
                                                  4-coumaric acid 39
                                                    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
                                                    Pestalotiopisorin A 0
                                                    bisdemethoxycurcumin 39
                                                    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