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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:citric acid
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Accession:CHEBI:30769 term browser browse the term
Definition:A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.
Synonyms:exact_synonym: 2-hydroxypropane-1,2,3-tricarboxylic acid
 related_synonym: 2-Hydroxy-1,2,3-propanetricarboxylic acid;   2-Hydroxytricarballylic acid;   3-Carboxy-3-hydroxypentane-1,5-dioic acid;   Citronensaeure;   E330;   Formula=C6H8O7;   H3cit;   InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);   InChIKey=KRKNYBCHXYNGOX-UHFFFAOYSA-N;   SMILES=OC(=O)CC(O)(CC(O)=O)C(O)=O
 alt_id: CHEBI:23322;   CHEBI:3727;   CHEBI:41523
 xref: BPDB:1359;   Beilstein:782061;   CAS:77-92-9;   DrugBank:DB04272;   Drug_Central:666;   Gmelin:4240;   HMDB:HMDB0000094;   KEGG:C00158;   KEGG:D00037;   KNApSAcK:C00007619
 xref_mesh: MESH:D019343
 xref: MetaCyc:CIT;   PDBeChem:CIT;   PMID:11762832;   PMID:11782123;   PMID:11857437;   PMID:14537820;   PMID:15311880;   PMID:15934243;   PMID:16232627;   PMID:17190852;   PMID:17357118;   PMID:17604395;   PMID:18298573;   PMID:18960216;   PMID:19288211;   PMID:22115968;   PMID:22192423;   PMID:22264346;   PMID:22373571;   PMID:22509852;   Reaxys:782061;   Wikipedia:Citric_Acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:133748;   is_conjugate_acid_of CHEBI:35804


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citric acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Aco2 aconitase 2 multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in decreased activity of ACO2 protein CTD PMID:16624386 NCBI chr 7:113,385,677...113,428,794
Ensembl chr 7:113,385,646...113,428,261 		JBrowse link
G Angptl3 angiopoietin-like 3 increases expression ISO Citric Acid results in increased expression of ANGPTL3 mRNA CTD PMID:27089845 NCBI chr 5:113,703,007...113,710,044
Ensembl chr 5:113,703,012...113,709,957 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in increased expression of BAX protein; [Silver analog co-treated with Citric Acid] results in increased expression of BAX mRNA CTD PMID:16624386 PMID:27021274 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 multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in decreased expression of BCL2 protein; [Silver analog co-treated with Citric Acid] results in increased expression of BCL2 mRNA CTD PMID:16624386 PMID:27021274 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 multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in decreased expression of BCL2L1 protein CTD PMID:16624386 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479 		JBrowse link
G Casp12 caspase 12 multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in increased activity of CASP12 protein CTD PMID:16624386 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 ISO [Citric Acid co-treated with zinc chloride] results in increased activity of CASP3 protein CTD PMID:16624386 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Cat catalase decreases activity
multiple interactions		 ISO Citric Acid results in decreased activity of CAT protein
Quercetin inhibits the reaction [Citric Acid results in decreased activity of CAT protein]		 CTD PMID:24745150 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions
decreases expression		 ISO [Silver analog co-treated with Citric Acid] results in increased secretion of CCL2 protein
Citric Acid results in decreased expression of CCL2 mRNA		 CTD PMID:27021274 PMID:37149095 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Ccnb1 cyclin B1 multiple interactions ISO [Silver analog co-treated with Citric Acid] results in decreased expression of CCNB1 mRNA CTD PMID:27021274 NCBI chr 2:31,912,190...31,921,163
Ensembl chr 2:31,912,193...31,921,172 		JBrowse link
G Cd86 CD86 molecule multiple interactions ISO Citric Acid inhibits the reaction [Dinitrochlorobenzene results in increased expression of CD86 protein]; Citric Acid inhibits the reaction [imidazolidinyl urea results in increased expression of CD86 protein] CTD PMID:29743441 NCBI chr11:64,142,193...64,200,816
Ensembl chr11:64,163,828...64,200,818 		JBrowse link
G Cdk2 cyclin dependent kinase 2 multiple interactions ISO [Silver analog co-treated with Citric Acid] affects the expression of CDK2 mRNA CTD PMID:27021274 NCBI chr 7:1,129,878...1,137,431
Ensembl chr 7:1,129,811...1,137,403 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in increased expression of CDKN1A protein CTD PMID:16624386 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cldn1 claudin 1 decreases expression ISO Citric Acid results in decreased expression of CLDN1 mRNA CTD PMID:37149095 NCBI chr11:74,421,569...74,436,728
Ensembl chr11:74,421,569...74,436,724 		JBrowse link
G Col2a1 collagen type II alpha 1 chain multiple interactions EXP [COL2A1 protein co-treated with Freund's Adjuvant] results in increased abundance of Citric Acid; [geniposide co-treated with phellodendrine co-treated with magnoflorine co-treated with Chlorogenic Acid co-treated with crocin co-treated with Flavonoids co-treated with Berberine Alkaloids] inhibits the reaction [[COL2A1 protein co-treated with Freund's Adjuvant] results in increased abundance of Citric Acid]; Dexamethasone inhibits the reaction [[COL2A1 protein co-treated with Freund's Adjuvant] results in increased abundance of Citric Acid]; huang-lien-chieh-tu-tang inhibits the reaction [[COL2A1 protein co-treated with Freund's Adjuvant] results in increased abundance of Citric Acid] CTD PMID:24709313 NCBI chr 7:129,098,489...129,127,560
Ensembl chr 7:129,098,786...129,127,546 		JBrowse link
G Dlg4 discs large MAGUK scaffold protein 4 multiple interactions EXP [Citric Acid co-treated with Silver analog] results in decreased expression of DLG4 protein CTD PMID:25447321 NCBI chr10:54,740,700...54,769,097
Ensembl chr10:54,739,470...54,767,153 		JBrowse link
G Ercc6 ERCC excision repair 6, chromatin remodeling factor decreases abundance ISO ERCC6 gene mutant form results in decreased abundance of Citric Acid CTD PMID:25440059 NCBI chr16:7,764,983...7,835,587
Ensembl chr16:7,765,013...7,835,587 		JBrowse link
G Ereg epiregulin decreases expression ISO Citric Acid results in decreased expression of EREG mRNA CTD PMID:37149095 NCBI chr14:17,027,287...17,041,062
Ensembl chr14:17,027,287...17,041,062 		JBrowse link
G Glud1 glutamate dehydrogenase 1 multiple interactions ISO Citric Acid inhibits the reaction [aluminum chloride binds to and results in decreased activity of GLUD1 protein] CTD PMID:14625697 NCBI chr16:9,640,312...9,673,961
Ensembl chr16:9,640,312...9,673,957 		JBrowse link
G Hlcs holocarboxylase synthetase decreases activity ISO Citric Acid results in decreased activity of HLCS protein CTD PMID:26303405 NCBI chr11:33,455,806...33,635,197
Ensembl chr11:33,455,809...33,624,222 		JBrowse link
G Icam1 intercellular adhesion molecule 1 multiple interactions
decreases expression		 ISO Citric Acid inhibits the reaction [Dinitrochlorobenzene results in increased expression of ICAM1 protein]; Citric Acid inhibits the reaction [imidazolidinyl urea results in increased expression of ICAM1 protein]
Citric Acid results in decreased expression of ICAM1 mRNA		 CTD PMID:29743441 PMID:37149095 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438 		JBrowse link
G Klk5 kallikrein related-peptidase 5 increases activity ISO Citric Acid results in increased activity of KLK5 protein CTD PMID:16517595 NCBI chr 1:94,296,574...94,304,768
Ensembl chr 1:94,296,168...94,304,666 		JBrowse link
G Lepr leptin receptor affects abundance ISO LEPR affects the abundance of Citric Acid CTD PMID:20567778 NCBI chr 5:116,294,409...116,477,904
Ensembl chr 5:116,289,823...116,475,908 		JBrowse link
G Lif LIF, interleukin 6 family cytokine decreases expression ISO Citric Acid results in decreased expression of LIF mRNA CTD PMID:37149095 NCBI chr14:79,131,049...79,140,486
Ensembl chr14:79,134,574...79,140,482 		JBrowse link
G Mir218-2 microRNA 218-2 increases expression ISO Citric Acid results in increased expression of MIR218-2 CTD PMID:37149095 NCBI chr10:20,068,451...20,068,560
Ensembl chr10:20,068,451...20,068,560 		JBrowse link
G Mkrn3 makorin, ring finger protein, 3 increases expression ISO Citric Acid results in increased expression of MKRN3 mRNA CTD PMID:37149095 NCBI chr 1:115,926,774...115,929,288
Ensembl chr 1:115,926,776...115,929,283 		JBrowse link
G Mt1 metallothionein 1 multiple interactions EXP [Silver analog co-treated with Citric Acid] results in increased expression of MT1A mRNA CTD PMID:25194297 NCBI chr19:10,826,032...10,827,048
Ensembl chr19:10,826,032...10,827,049
Ensembl chr17:10,826,032...10,827,049 		JBrowse link
G Muc5ac mucin 5AC, oligomeric mucus/gel-forming multiple interactions
increases secretion		 ISO Capsaicin promotes the reaction [Citric Acid results in increased secretion of MUC5AC protein]; capsazepine inhibits the reaction [Citric Acid results in increased secretion of MUC5AC protein] CTD PMID:22566028 NCBI chr 1:196,864,336...196,896,475
Ensembl chr 1:196,864,336...196,896,475 		JBrowse link
G Nr1h4 nuclear receptor subfamily 1, group H, member 4 multiple interactions ISO [[NR1H4 protein co-treated with Dietary Fats] results in increased susceptibility to caffeic acid phenethyl ester] which results in increased abundance of Citric Acid CTD PMID:28223344 NCBI chr 7:23,846,122...23,942,085
Ensembl chr 7:23,846,122...23,942,047 		JBrowse link
G Pfkm phosphofructokinase, muscle multiple interactions ISO Citric Acid promotes the reaction [resveratrol results in decreased activity of PFKM protein] CTD PMID:23454376 NCBI chr 7:129,221,679...129,259,192
Ensembl chr 7:129,221,653...129,259,192 		JBrowse link
G Serpinb2 serpin family B member 2 decreases expression ISO Citric Acid results in decreased expression of SERPINB2 mRNA CTD PMID:37149095 NCBI chr13:23,537,312...23,551,823
Ensembl chr13:23,541,400...23,550,408 		JBrowse link
G Slc13a2 solute carrier family 13 member 2 increases uptake
multiple interactions		 ISO
EXP		 SLC13A2 protein results in increased uptake of Citric Acid
Lithium promotes the reaction [SLC13A2 protein results in increased uptake of Citric Acid]
Lithium inhibits the reaction [SLC13A2 protein results in increased uptake of Citric Acid]		 CTD PMID:12826022 NCBI chr10:63,291,813...63,319,127
Ensembl chr10:63,291,815...63,319,127 		JBrowse link
G Slc13a5 solute carrier family 13 member 5 affects uptake ISO SLC13A5 protein affects the uptake of Citric Acid CTD PMID:30054523 NCBI chr10:56,866,249...56,891,189
Ensembl chr10:56,866,249...56,890,945 		JBrowse link
G Slco1a4 solute carrier organic anion transporter family, member 1a4 affects abundance ISO SLCO1A4 protein affects the abundance of Citric Acid CTD PMID:21561886 NCBI chr 4:174,710,004...174,764,810
Ensembl chr 4:174,710,004...175,254,573 		JBrowse link
G Smad6 SMAD family member 6 increases expression ISO Citric Acid results in increased expression of SMAD6 mRNA CTD PMID:37149095 NCBI chr 8:64,450,114...64,519,673
Ensembl chr 8:64,450,114...64,519,763 		JBrowse link
G Syn1 synapsin I multiple interactions EXP [Citric Acid co-treated with Silver analog] results in decreased expression of SYN1 protein CTD PMID:25447321 NCBI chr  X:1,172,208...1,227,400
Ensembl chr  X:1,172,208...1,227,396 		JBrowse link
G Syp synaptophysin multiple interactions EXP [Citric Acid co-treated with Silver analog] results in decreased expression of SYP protein CTD PMID:25447321 NCBI chr  X:14,849,444...14,864,553
Ensembl chr  X:14,849,444...14,864,745 		JBrowse link
G Tert telomerase reverse transcriptase multiple interactions ISO [Citric Acid co-treated with zinc chloride] results in decreased activity of TERT protein CTD PMID:16624386 NCBI chr 1:29,637,213...29,659,561
Ensembl chr 1:29,637,506...29,659,561 		JBrowse link
G Tf transferrin multiple interactions ISO Citric Acid promotes the reaction [Chromium binds to TF protein] CTD PMID:1375080 NCBI chr 8:103,789,780...103,816,487
Ensembl chr 8:103,767,995...103,816,511 		JBrowse link
G Tnfaip2 TNF alpha induced protein 2 decreases expression ISO Citric Acid results in decreased expression of TNFAIP2 mRNA CTD PMID:37149095 NCBI chr 6:130,476,832...130,489,914
Ensembl chr 6:130,476,889...130,489,914 		JBrowse link
G Trpv1 transient receptor potential cation channel, subfamily V, member 1 multiple interactions
increases activity		 ISO capsazepine inhibits the reaction [Citric Acid results in increased activity of TRPV1 protein] CTD PMID:22566028 NCBI chr10:57,851,428...57,876,513
Ensembl chr10:57,851,428...57,876,513 		JBrowse link
G Vegfa vascular endothelial growth factor A affects binding ISO VEGFA protein binds to Citric Acid analog CTD PMID:22154009 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19922
    role 19894
      biological role 19864
        antimicrobial agent 18270
          citric acid 42
            (3S)-citryl-CoA 0
            2-[(L-alanin-3-ylcarbamoyl)methyl]-2-hydroxybutanedioate(2-) 0
            2-methylcitric acid + 0
            Anaerocult(TM) 0
            N(alpha)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine 0
            beta-citryl-Glu-Glu 0
            beta-citrylglutamic acid 0
            iron(III) dicitrate(3-) 0
            rhizobactin 1021 0
            schizokinen 0
            staphyloferrin A + 0
            staphyloferrin B 0
            vibrioferrin 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19922
    subatomic particle 19892
      composite particle 19892
        hadron 19920
          baryon 19892
            nucleon 19920
              atomic nucleus 19892
                atom 19892
                  main group element atom 19866
                    p-block element atom 19866
                      carbon group element atom 19805
                        carbon atom 19802
                          organic molecular entity 19775
                            heteroorganic entity 19556
                              organochalcogen compound 19315
                                organooxygen compound 19205
                                  carbon oxoacid 18694
                                    carboxylic acid 18691
                                      tricarboxylic acid 2505
                                        citric acid 42
                                          (3S)-citryl-CoA 0
                                          2-[(L-alanin-3-ylcarbamoyl)methyl]-2-hydroxybutanedioate(2-) 0
                                          2-methylcitric acid + 0
                                          Anaerocult(TM) 0
                                          N(alpha)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine 0
                                          beta-citryl-Glu-Glu 0
                                          beta-citrylglutamic acid 0
                                          iron(III) dicitrate(3-) 0
                                          rhizobactin 1021 0
                                          schizokinen 0
                                          staphyloferrin A + 0
                                          staphyloferrin B 0
                                          vibrioferrin 0
paths to the root