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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:3,4-dihydroxybenzoic acid
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Accession:CHEBI:36062 term browser browse the term
Definition:A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.
Synonyms:related_synonym: 4,5-Dihydroxybenzoic acid;   4-Carboxy-1,2-dihydroxybenzene;   Formula=C7H6O4;   InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11);   InChIKey=YQUVCSBJEUQKSH-UHFFFAOYSA-N;   Protocatechuic acid;   Protocatehuic acid;   SMILES=C(=O)(C1=CC(=C(C=C1)O)O)O
 alt_id: CHEBI:1380;   CHEBI:16798;   CHEBI:19879;   CHEBI:20270;   CHEBI:20272;   CHEBI:41912
 xref: CAS:99-50-3;   HMDB:HMDB0001856;   KEGG:C00230;   KNApSAcK:C00002668
 xref_mesh: MESH:C009091
 xref: MetaCyc:3-4-DIHYDROXYBENZOATE;   PDBeChem:DHB;   PMID:17709440;   PMID:19160570;   PMID:20840540;   PMID:20973550;   PMID:21569764;   PMID:21619045;   PMID:22770225;   Reaxys:1448841;   Wikipedia:Protocatechuic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:36241


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3,4-dihydroxybenzoic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr1b1 aldo-keto reductase family 1 member B multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in increased expression of AKR1B3 mRNA] CTD PMID:22687555 NCBI chr 4:61,706,866...61,720,959
Ensembl chr 4:61,706,864...61,720,956
JBrowse link
G App amyloid beta precursor protein multiple interactions ISO Gallic Acid inhibits the reaction [protocatechuic acid inhibits the reaction [APP protein modified form binds to APP protein modified form]]; protocatechuic acid inhibits the reaction [APP protein modified form binds to APP protein modified form] CTD PMID:22129351 NCBI chr11:24,425,013...24,641,872
Ensembl chr11:24,425,005...24,641,858
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions EXP protocatechuic acid inhibits the reaction [Rotenone results in decreased expression of BCL2 protein] CTD PMID:18082360 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions EXP protocatechuic acid inhibits the reaction [Rotenone results in increased activity of CASP3 protein] CTD PMID:18082360 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Cat catalase increases activity EXP protocatechuic acid results in increased activity of CAT protein CTD PMID:29842870 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO protocatechuic acid inhibits the reaction [Lipopolysaccharides results in increased secretion of CCL2 protein] CTD PMID:31306686 NCBI chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression EXP protocatechuic acid results in increased expression of CDKN1A protein CTD PMID:16227210 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Comt catechol-O-methyltransferase increases methylation ISO
EXP
COMT protein results in increased methylation of protocatechuic acid CTD PMID:11160877 NCBI chr11:86,715,981...86,735,630
Ensembl chr11:86,715,981...86,735,622
JBrowse link
G Cs citrate synthase increases activity ISO protocatechuic acid results in increased activity of CS protein CTD PMID:31306686 NCBI chr 7:2,752,680...2,778,963
Ensembl chr 7:2,752,680...2,778,963
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions EXP protocatechuic acid inhibits the reaction [Methylcholanthrene results in increased activity of CYP1A1 protein] CTD PMID:15302093 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 multiple interactions EXP protocatechuic acid inhibits the reaction [Methylcholanthrene results in increased activity of CYP1A2 protein] CTD PMID:15302093 NCBI chr 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions
decreases activity
EXP [protocatechuic acid co-treated with Methylcholanthrene] results in decreased activity of CYP2E1 protein
protocatechuic acid results in decreased activity of CYP2E1 protein
CTD PMID:15302093 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Eno1 enolase 1 increases expression ISO protocatechuic acid results in increased expression of ENO1 mRNA CTD PMID:16227210 NCBI chr 5:167,288,223...167,299,610
Ensembl chr 5:167,288,223...167,299,609
JBrowse link
G Epo erythropoietin increases expression
multiple interactions
EXP protocatechuic acid results in increased expression of EPO protein
protocatechuic acid inhibits the reaction [methylmercuric chloride results in decreased expression of EPO protein]; protocatechuic acid inhibits the reaction [Methylmercury Compounds results in decreased expression of EPO protein]
CTD PMID:31850806, PMID:32461003 NCBI chr12:22,274,828...22,278,268
Ensembl chr12:22,274,828...22,278,266
JBrowse link
G Fshb follicle stimulating hormone subunit beta increases expression EXP protocatechuic acid results in increased expression of FSHB protein CTD PMID:29842870 NCBI chr 3:98,088,321...98,092,131
Ensembl chr 3:98,088,324...98,092,131
JBrowse link
G G6pd glucose-6-phosphate dehydrogenase increases activity EXP protocatechuic acid results in increased activity of G6PD protein CTD PMID:29842870 NCBI chr  X:156,274,800...156,293,935
Ensembl chr  X:156,274,800...156,293,926
JBrowse link
G Glo1 glyoxalase 1 multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in decreased expression of and results in decreased activity of GLO1 protein] CTD PMID:22687555 NCBI chr20:9,273,589...9,291,608
Ensembl chr20:9,273,594...9,291,610
JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha increases stability
increases expression
multiple interactions
EXP protocatechuic acid results in increased stability of HIF1A protein
protocatechuic acid results in increased expression of HIF1A protein
protocatechuic acid inhibits the reaction [methylmercuric chloride results in decreased expression of HIF1A protein]; protocatechuic acid inhibits the reaction [Methylmercury Compounds results in decreased expression of HIF1A protein]
CTD PMID:16227210, PMID:31850806, PMID:32461003 NCBI chr 6:96,810,868...96,856,303
Ensembl chr 6:96,810,907...96,856,052
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in increased secretion of IL1B protein] CTD PMID:22687555 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Il6 interleukin 6 multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in increased secretion of IL6 protein] CTD PMID:22687555 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Ldhc lactate dehydrogenase C increases activity EXP protocatechuic acid results in increased activity of LDHC protein CTD PMID:29842870 NCBI chr 1:102,914,875...102,931,843
Ensembl chr 1:102,915,191...102,931,839
JBrowse link
G Lhb luteinizing hormone subunit beta increases expression EXP protocatechuic acid results in increased expression of LHB protein CTD PMID:29842870 NCBI chr 1:101,409,992...101,413,725
Ensembl chr 1:101,410,019...101,413,724
JBrowse link
G Mpo myeloperoxidase increases activity
decreases activity
ISO
EXP
protocatechuic acid results in increased activity of MPO protein
protocatechuic acid results in decreased activity of MPO protein
CTD PMID:24060682, PMID:29842870 NCBI chr10:75,087,892...75,098,260
Ensembl chr10:75,087,892...75,098,260
JBrowse link
G Nfkbib NFKB inhibitor beta multiple interactions ISO protocatechuic acid inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of and results in increased activity of NFKBIB protein] CTD PMID:20026373 NCBI chr 1:86,941,073...86,948,845
Ensembl chr 1:86,941,074...86,948,845
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO protocatechuic acid inhibits the reaction [[Tetradecanoylphorbol Acetate results in increased expression of NOS2 protein] which results in increased abundance of Nitrites]; protocatechuic acid inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein]; protocatechuic acid inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of NOS2 protein] CTD PMID:20026373, PMID:31306686 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 multiple interactions
increases activity
EXP [protocatechuic acid co-treated with Methylcholanthrene] results in increased activity of NQO1 protein
protocatechuic acid results in increased activity of NQO1 protein
CTD PMID:15302093 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in increased expression of PTGS2 mRNA]; protocatechuic acid inhibits the reaction [Galactose results in increased expression of PTGS2 protein]; protocatechuic acid inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 protein]; protocatechuic acid inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of and results in increased expression of PTGS2 protein] CTD PMID:20026373, PMID:22687555, PMID:31306686 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in increased expression of and results in increased activity of RELA protein]; protocatechuic acid inhibits the reaction [Galactose results in increased expression of RELA mRNA]; protocatechuic acid inhibits the reaction [Galactose results in increased expression of RELA protein]; protocatechuic acid inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of RELA protein] CTD PMID:20026373, PMID:22687555 NCBI chr 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
JBrowse link
G Sele selectin E multiple interactions ISO protocatechuic acid inhibits the reaction [TNF protein results in increased expression of SELE protein] CTD PMID:30611791 NCBI chr13:82,355,234...82,365,323
Ensembl chr13:82,355,471...82,365,341
JBrowse link
G Slc2a1 solute carrier family 2 member 1 increases expression
multiple interactions
EXP protocatechuic acid results in increased expression of SLC2A1 protein
protocatechuic acid inhibits the reaction [methylmercuric chloride results in decreased expression of SLC2A1 protein]; protocatechuic acid inhibits the reaction [Methylmercury Compounds results in decreased expression of SLC2A1 protein]
CTD PMID:31850806, PMID:32461003 NCBI chr 5:138,154,677...138,182,897
Ensembl chr 5:138,154,673...138,182,897
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO protocatechuic acid inhibits the reaction [Galactose results in increased secretion of TNF protein]; protocatechuic acid inhibits the reaction [Lipopolysaccharides results in increased secretion of TNF protein]
protocatechuic acid inhibits the reaction [TNF protein results in increased expression of SELE protein]
CTD PMID:22687555, PMID:30611791, PMID:31306686 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 increases expression
multiple interactions
EXP protocatechuic acid results in increased expression of VEGFA protein
protocatechuic acid inhibits the reaction [methylmercuric chloride results in decreased expression of VEGFA protein]; protocatechuic acid inhibits the reaction [Methylmercury Compounds results in decreased expression of VEGFA protein]
CTD PMID:16227210, PMID:31850806, PMID:32461003 NCBI chr 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
JBrowse link
ethyl 3,4-dihydroxybenzoate term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Fabp4 fatty acid binding protein 4 multiple interactions ISO ethyl protocatechuate inhibits the reaction [rosiglitazone results in increased expression of FABP4 mRNA] CTD PMID:24338020 NCBI chr 2:93,792,666...93,797,267
Ensembl chr 2:93,792,601...93,797,305
JBrowse link
G Gata3 GATA binding protein 3 multiple interactions ISO ethyl protocatechuate inhibits the reaction [rosiglitazone results in increased ubiquitination of and results in increased degradation of GATA3 protein] CTD PMID:24338020 NCBI chr17:72,419,752...72,452,043
Ensembl chr17:72,429,618...72,450,681
JBrowse link
G Klf2 Kruppel-like factor 2 multiple interactions ISO ethyl protocatechuate inhibits the reaction [rosiglitazone results in increased ubiquitination of and results in increased degradation of KLF2 protein] CTD PMID:24338020 NCBI chr16:19,223,087...19,225,037
Ensembl chr16:19,223,087...19,225,037
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions ISO ethyl protocatechuate inhibits the reaction [rosiglitazone results in increased expression of PPARG mRNA] CTD PMID:24338020 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Sp7 Sp7 transcription factor multiple interactions ISO ethyl protocatechuate inhibits the reaction [Ascorbic Acid results in increased expression of SP7 mRNA]; ethyl protocatechuate inhibits the reaction [Ascorbic Acid results in increased expression of SP7 protein] CTD PMID:21467157 NCBI chr 7:143,957,316...143,967,488
Ensembl chr 7:143,958,858...143,967,484
JBrowse link
G Taz tafazzin multiple interactions ISO ethyl protocatechuate inhibits the reaction [rosiglitazone results in increased ubiquitination of and results in increased degradation of TAZ protein] CTD PMID:24338020 NCBI chr  X:156,421,006...156,429,461
Ensembl chr  X:156,421,009...156,428,593
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      biological role 19732
        antimicrobial agent 17309
          antimicrobial food preservative 11603
            benzoic acid 3839
              3,4-dihydroxybenzoic acid 38
                1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose + 0
                ethyl 3,4-dihydroxybenzoate 6
                methyl 3,4-dihydroxybenzoate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            organic group 18493
                              organic divalent group 18486
                                organodiyl group 18486
                                  carbonyl group 18389
                                    carbonyl compound 18389
                                      carboxylic acid 18060
                                        aromatic carboxylic acid 10889
                                          benzoic acids 10858
                                            benzoic acid 3839
                                              hydroxybenzoic acid 3227
                                                dihydroxybenzoic acid 48
                                                  3,4-dihydroxybenzoic acid 38
                                                    1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose + 0
                                                    ethyl 3,4-dihydroxybenzoate 6
                                                    methyl 3,4-dihydroxybenzoate 0
paths to the root

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.