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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;   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


show annotations for term's descendants           Sort by:
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 7:115,265,816...115,308,931
Ensembl chr 7:115,265,791...115,308,892 		JBrowse link
G Angptl3 angiopoietin-like 3 increases expression ISO Citric Acid results in increased expression of ANGPTL3 mRNA CTD PMID:27089845 NCBI chr 5:118,818,494...118,825,531
Ensembl chr 5:118,818,499...118,826,444 		JBrowse link
G App amyloid beta precursor protein multiple interactions
decreases abundance 		ISO [APP protein mutant form co-treated with PSEN1 protein mutant form] results in decreased abundance of Citric Acid; PF-06840003 inhibits the reaction [[APP protein mutant form co-treated with PSEN1 protein mutant form] results in decreased abundance of Citric Acid]
APP protein mutant form results in decreased abundance of Citric Acid
PF-06840003 inhibits the reaction [APP protein mutant form results in decreased abundance of Citric Acid] 		CTD PMID:39172838 NCBI chr11:37,506,207...37,724,351
Ensembl chr11:37,506,408...37,722,971 		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 1:105,076,472...105,081,906
Ensembl chr 1:105,076,473...105,086,429 		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 chr13:23,204,464...23,366,900
Ensembl chr13:23,204,464...23,366,900 		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 3:161,713,777...161,764,844
Ensembl chr 3:161,745,540...161,764,907
Ensembl chr 1:161,745,540...161,764,907 		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 8:10,927,188...10,954,442
Ensembl chr 8:10,926,994...10,954,442 		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 chr16:52,395,539...52,413,794
Ensembl chr16:52,395,540...52,413,732 		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 3:110,297,340...110,329,526
Ensembl chr 3:110,297,342...110,329,526 		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 chr10:67,503,077...67,504,875
Ensembl chr10:67,503,077...67,504,875 		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 2:33,646,252...33,655,225
Ensembl chr 2:33,646,252...33,655,225 		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 chr11:77,647,565...77,706,178
Ensembl chr11:77,647,600...77,725,361 		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 7:1,714,392...1,721,964
Ensembl chr 7:1,714,392...1,721,878 		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 chr20:7,150,820...7,161,373
Ensembl chr20:7,153,958...7,164,969 		JBrowse link
G Cldn1 claudin 1 decreases expression ISO Citric Acid results in decreased expression of CLDN1 mRNA CTD PMID:37149095 NCBI chr11:87,926,376...87,941,533
Ensembl chr11:87,926,337...87,941,529 		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 7:130,977,561...131,006,627
Ensembl chr 7:130,977,561...131,006,627 		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 chr10:55,239,397...55,267,780
Ensembl chr10:55,236,869...55,265,839 		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 chr16:7,771,311...7,841,895
Ensembl chr16:7,771,581...7,841,895 		JBrowse link
G Ereg epiregulin decreases expression ISO Citric Acid results in decreased expression of EREG mRNA CTD PMID:37149095 NCBI chr14:17,311,485...17,325,260
Ensembl chr14:17,311,485...17,325,260 		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 chr16:9,646,569...9,680,215
Ensembl chr16:9,646,509...9,680,210 		JBrowse link
G Hlcs holocarboxylase synthetase decreases activity ISO Citric Acid results in decreased activity of HLCS protein CTD PMID:26303405 NCBI chr11:46,925,491...47,123,111
Ensembl chr11:46,925,491...47,105,082 		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 8:27,829,688...27,841,618
Ensembl chr 8:27,829,161...27,841,617 		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 1:103,432,743...103,442,011
Ensembl chr 1:103,433,065...103,441,305 		JBrowse link
G Lepr leptin receptor affects abundance ISO LEPR affects the abundance of Citric Acid CTD PMID:20567778 NCBI chr 5:121,409,735...121,593,201
Ensembl chr 5:121,474,099...121,591,215 		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 chr14:83,354,602...83,364,053
Ensembl chr14:83,358,164...83,364,053 		JBrowse link
G Mapt microtubule-associated protein tau multiple interactions
decreases abundance 		ISO PF-06840003 inhibits the reaction [MAPT protein mutant form results in decreased abundance of Citric Acid] CTD PMID:39172838 NCBI chr10:89,638,618...89,736,108
Ensembl chr10:89,638,599...89,736,108 		JBrowse link
G Mir218-2 microRNA 218-2 increases expression ISO Citric Acid results in increased expression of MIR218-2 CTD PMID:37149095 NCBI chr10:20,572,523...20,572,632
Ensembl chr10:20,572,523...20,572,632 		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 1:125,338,664...125,341,178
Ensembl chr 1:125,338,564...125,341,164 		JBrowse link
G Mt1a metallothionein 1A multiple interactions EXP [Silver analog co-treated with Citric Acid] results in increased expression of MT1A mRNA CTD PMID:25194297 NCBI chr19:10,831,959...10,832,975
Ensembl chr17:79,695,809...79,696,200
Ensembl chr  X:79,695,809...79,696,200
Ensembl chr19:79,695,809...79,696,200 		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 1:206,293,717...206,326,006
Ensembl chr 1:206,293,869...206,326,006 		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 7:25,733,471...25,829,440
Ensembl chr 7:25,733,471...25,829,389 		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 7:131,100,684...131,138,250
Ensembl chr 7:131,100,753...131,138,248 		JBrowse link
G Psen1 presenilin 1 multiple interactions ISO [APP protein mutant form co-treated with PSEN1 protein mutant form] results in decreased abundance of Citric Acid; PF-06840003 inhibits the reaction [[APP protein mutant form co-treated with PSEN1 protein mutant form] results in decreased abundance of Citric Acid] CTD PMID:39172838 NCBI chr 6:109,054,160...109,106,191
Ensembl chr 6:109,060,352...109,106,189 		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 chr13:24,051,933...24,065,032
Ensembl chr13:24,056,021...24,065,031 		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 chr10:63,789,874...63,817,441
Ensembl chr10:63,789,876...63,817,184 		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 chr10:57,364,806...57,389,500
Ensembl chr10:57,364,806...57,389,516 		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 4:176,441,104...176,495,846
Ensembl chr 4:176,441,104...176,495,816 		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 8:73,345,457...73,414,985
Ensembl chr 8:73,345,460...73,414,149 		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:3,725,745...3,780,940
Ensembl chr  X:3,725,714...3,780,938 		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:17,521,348...17,536,449
Ensembl chr  X:17,521,348...17,536,984 		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 1:31,465,766...31,488,650
Ensembl chr 1:31,466,056...31,488,111 		JBrowse link
G Tf transferrin multiple interactions ISO Citric Acid promotes the reaction [Chromium binds to TF protein] CTD PMID:1375080 NCBI chr 8:112,668,667...112,695,376
Ensembl chr 8:112,647,642...112,695,400 		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 6:136,297,388...136,311,106
Ensembl chr 6:136,298,082...136,311,106 		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 chr10:58,349,936...58,375,021
Ensembl chr10:58,340,223...58,375,021 		JBrowse link
G Vegfa vascular endothelial growth factor A affects binding ISO VEGFA protein binds to Citric Acid analog CTD PMID:22154009 NCBI chr 9:22,452,854...22,468,194
Ensembl chr 9:22,439,392...22,468,194 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20871
    role 20829
      biological role 20827
        antimicrobial agent 18581
          citric acid 45
            (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 20871
    subatomic particle 20869
      composite particle 20869
        hadron 20869
          baryon 20869
            nucleon 20869
              atomic nucleus 20869
                atom 20869
                  main group element atom 20792
                    p-block element atom 20792
                      carbon group element atom 20725
                        carbon atom 20721
                          organic molecular entity 20721
                            heteroorganic entity 20226
                              organochalcogen compound 19911
                                organooxygen compound 19814
                                  carbon oxoacid 19160
                                    carboxylic acid 19157
                                      tricarboxylic acid 2537
                                        citric acid 45
                                          (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