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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:gamma-linolenic acid
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Accession:CHEBI:28661 term browser browse the term
Definition:A C18, ω-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.
Synonyms:related_synonym: (6,9,12)-linolenic acid;   (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid;   (Z,Z,Z)-6,9,12-octadecatrienoic acid;   18:3 (n-6);   6,9,12-Octadecatrienoic acid;   6-cis,9-cis,12-cis-octadecatrienoic acid;   6Z,9Z,12Z-Octadecatrienoic acid;   C18:3 (n-6);   C18:3, n-6,9,12 all-cis;   GLA;   Octadeca-6,9,12-triensaeure;   all-cis-6,9,12-octadecatrienoic acid;   cis-Delta(6,9,12)-octadecatrienoic acid;   gamma-Linolensaeure;   gamoleic acid;   gamolenic acid
 alt_id: CHEBI:10573;   CHEBI:24197
 xref: CAS:506-26-3;   HMDB:HMDB0003073;   KNApSAcK:C00001226
 xref_mesh: MESH:D017965
 xref: Reaxys:1712253;   drugcentral:1276;   kegg.compound:C06426;   kegg.drug:D07213;   lipidmaps:LMFA01030141;   metacyc.compound:CPD-8117;   pubmed:11385052;   pubmed:24435467;   pubmed:9732298;   wikipedia.en:Gamma-Linolenic_acid
 chemrof_formula: C18H30O2
 chemrof_smiles: CCCCC/C=CC/C=CC/C=CCCCCC(=O)O
 chemrof_inchi: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
 chemrof_inchikey: VZCCETWTMQHEPK-QNEBEIHSSA-N
 cyclic_relationship: is_conjugate_acid_of CHEBI:32391


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gamma-linolenic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr1c1 aldo-keto reductase family 1, member C1 increases expression ISO gamma-Linolenic Acid results in increased expression of AKR1C1 mRNA CTD PMID:20664735 NCBI chr17:70,720,397...70,747,285
Ensembl chr17:70,720,398...70,747,247 		JBrowse link
G Apoh apolipoprotein H decreases expression ISO gamma-Linolenic Acid results in decreased expression of APOH mRNA CTD PMID:20664735 NCBI chr10:93,841,992...93,855,897
Ensembl chr10:93,841,966...93,857,127 		JBrowse link
G Ar androgen receptor multiple interactions ISO gamma-Linolenic Acid inhibits the reaction [Metribolone results in increased activity of AR protein] CTD PMID:18324785 NCBI chr  X:67,135,317...67,304,476
Ensembl chr  X:67,135,317...67,304,467 		JBrowse link
G Asah1 N-acylsphingosine amidohydrolase 1 increases expression ISO gamma-Linolenic Acid results in increased expression of ASAH1 mRNA CTD PMID:20664735 NCBI chr16:57,669,927...57,701,349
Ensembl chr16:57,669,750...57,718,305 		JBrowse link
G Casp3 caspase 3 increases activity ISO gamma-Linolenic Acid results in increased activity of CASP3 protein CTD PMID:16857180 NCBI chr16:52,395,539...52,413,794
Ensembl chr16:52,395,540...52,413,732 		JBrowse link
G Ccna2 cyclin A2 decreases expression ISO gamma-Linolenic Acid results in decreased expression of CCNA2 protein CTD PMID:15318936 NCBI chr 2:121,355,363...121,361,762
Ensembl chr 2:121,355,363...121,361,701 		JBrowse link
G Ccne1 cyclin E1 decreases expression ISO gamma-Linolenic Acid results in decreased expression of CCNE1 protein CTD PMID:15318936 NCBI chr 1:99,918,672...99,927,986
Ensembl chr 1:99,918,674...99,927,822 		JBrowse link
G Cdk1 cyclin-dependent kinase 1 decreases expression ISO gamma-Linolenic Acid results in decreased expression of CDK1 protein CTD PMID:15318936 NCBI chr20:19,265,252...19,280,456
Ensembl chr20:19,265,289...19,280,455 		JBrowse link
G Cldn5 claudin 5 multiple interactions ISO [gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of CLDN5 protein; [gamma-Linolenic Acid co-treated with Iodine] results in increased expression of and results in increased localization of CLDN5 protein; [Selenium co-treated with gamma-Linolenic Acid] results in increased expression of and results in increased localization of CLDN5 protein; gamma-Linolenic Acid results in increased expression of and results in increased localization of CLDN5 protein CTD PMID:16514648 NCBI chr11:95,717,172...95,718,598
Ensembl chr11:95,717,176...95,719,322 		JBrowse link
G Clta clathrin, light chain A increases expression ISO gamma-Linolenic Acid results in increased expression of CLTA mRNA CTD PMID:20664735 NCBI chr 5:63,022,046...63,059,223
Ensembl chr 5:63,041,184...63,059,215 		JBrowse link
G Fth1 ferritin heavy chain 1 increases expression ISO gamma-Linolenic Acid results in increased expression of FTH1 mRNA CTD PMID:20664735 NCBI chr 1:216,052,037...216,054,325
Ensembl chr 1:216,051,998...216,055,214 		JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit increases activity
increases expression 		ISO gamma-Linolenic Acid results in increased activity of GCLC protein
gamma-Linolenic Acid results in increased expression of GCLC mRNA 		CTD PMID:17092368 NCBI chr 8:87,510,251...87,548,896
Ensembl chr 8:87,510,463...87,548,893 		JBrowse link
G Grk5 G protein-coupled receptor kinase 5 increases expression ISO gamma-Linolenic Acid results in increased expression of GRK5 mRNA CTD PMID:20664735 NCBI chr 1:270,014,314...270,208,294
Ensembl chr 1:270,014,282...270,204,928 		JBrowse link
G H2ac6 H2A clustered histone 6 decreases expression ISO gamma-Linolenic Acid results in decreased expression of H2AC6 mRNA CTD PMID:20664735 NCBI chr17:47,403,701...47,404,167 JBrowse link
G Hexb hexosaminidase subunit beta increases expression ISO gamma-Linolenic Acid results in increased expression of HEXB mRNA CTD PMID:20664735 NCBI chr 2:30,218,608...30,238,771
Ensembl chr 2:30,218,608...30,238,771 		JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO gamma-Linolenic Acid results in increased expression of HMOX1 mRNA; gamma-Linolenic Acid results in increased expression of HMOX1 protein CTD PMID:17092368 PMID:20664735 NCBI chr19:13,452,365...13,479,823
Ensembl chr19:13,472,884...13,479,818 		JBrowse link
G Il2 interleukin 2 affects expression ISO gamma-Linolenic Acid affects the expression of IL2 protein CTD PMID:9415022 NCBI chr 2:121,932,968...121,937,672
Ensembl chr 2:121,932,968...121,937,672 		JBrowse link
G Junb JunB proto-oncogene, AP-1 transcription factor subunit decreases expression ISO gamma-Linolenic Acid results in decreased expression of JUNB protein CTD PMID:15318936 NCBI chr19:40,081,126...40,082,910
Ensembl chr19:40,073,541...40,085,218 		JBrowse link
G Kynu kynureninase decreases expression ISO gamma-Linolenic Acid results in decreased expression of KYNU mRNA CTD PMID:20664735 NCBI chr 3:48,188,286...48,338,996
Ensembl chr 3:48,188,182...48,339,014 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 decreases expression ISO gamma-Linolenic Acid results in decreased expression of MAPK3 protein CTD PMID:15318936 NCBI chr 1:190,797,189...190,803,411
Ensembl chr 1:190,797,185...190,803,411 		JBrowse link
G Mmp11 matrix metallopeptidase 11 decreases expression ISO gamma-Linolenic Acid results in decreased expression of MMP11 mRNA CTD PMID:20664735 NCBI chr20:12,730,284...12,739,067
Ensembl chr20:12,730,277...12,739,290 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases expression ISO gamma-Linolenic Acid results in decreased expression of MYC protein CTD PMID:15318936 NCBI chr 7:95,483,105...95,488,031
Ensembl chr 7:95,483,105...95,488,028 		JBrowse link
G Ocln occludin multiple interactions ISO [gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of OCLN protein; [gamma-Linolenic Acid co-treated with Iodine] results in increased expression of and results in increased localization of OCLN protein; [Selenium co-treated with gamma-Linolenic Acid] results in increased expression of and results in increased localization of OCLN protein; gamma-Linolenic Acid results in increased expression of and results in increased localization of OCLN protein CTD PMID:16514648 NCBI chr 2:33,391,303...33,442,207
Ensembl chr 2:33,391,303...33,430,411 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO gamma-Linolenic Acid results in increased cleavage of PARP1 protein CTD PMID:10403056 NCBI chr13:94,839,484...94,871,295
Ensembl chr13:94,839,433...94,871,567 		JBrowse link
G Pcna proliferating cell nuclear antigen decreases expression ISO gamma-Linolenic Acid results in decreased expression of PCNA mRNA CTD PMID:20664735 NCBI chr 3:139,951,948...139,955,820
Ensembl chr 3:139,951,941...139,955,901 		JBrowse link
G Pdlim1 PDZ and LIM domain 1 decreases expression ISO gamma-Linolenic Acid results in decreased expression of PDLIM1 mRNA CTD PMID:20664735 NCBI chr 1:248,991,818...249,040,409
Ensembl chr 1:248,991,818...249,047,379 		JBrowse link
G Plin2 perilipin 2 increases expression ISO gamma-Linolenic Acid results in increased expression of PLIN2 mRNA CTD PMID:20664735 NCBI chr 5:106,202,634...106,258,748
Ensembl chr 5:106,202,634...106,258,878 		JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions ISO gamma-Linolenic Acid binds to and results in increased activity of PPARA protein CTD PMID:10403814 NCBI chr 7:118,712,261...118,780,723
Ensembl chr 7:118,712,412...118,780,714 		JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions ISO gamma-Linolenic Acid binds to and results in increased activity of PPARG protein CTD PMID:15318936 NCBI chr 4:150,095,743...150,221,104
Ensembl chr 4:150,095,787...150,221,104 		JBrowse link
G Ptgr1 prostaglandin reductase 1 increases expression ISO gamma-Linolenic Acid results in increased expression of PTGR1 mRNA CTD PMID:20664735 NCBI chr 5:78,579,060...78,597,671
Ensembl chr 5:78,579,057...78,597,811 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 increases expression ISO gamma-Linolenic Acid results in increased expression of PTGS2 mRNA CTD PMID:17092368 NCBI chr13:64,714,063...64,722,320
Ensembl chr13:64,713,619...64,722,320 		JBrowse link
G Skp2 S-phase kinase associated protein 2 decreases expression ISO gamma-Linolenic Acid results in decreased expression of SKP2 mRNA CTD PMID:20664735 NCBI chr 2:59,888,406...59,916,471
Ensembl chr 2:59,888,413...59,916,438 		JBrowse link
G Slc3a2 solute carrier family 3 member 2 increases expression ISO gamma-Linolenic Acid results in increased expression of SLC3A2 mRNA CTD PMID:20664735 NCBI chr 1:215,033,601...215,048,064
Ensembl chr 1:215,033,601...215,048,064 		JBrowse link
G St13 ST13, Hsp70 interacting protein increases expression ISO gamma-Linolenic Acid results in increased expression of ST13 mRNA CTD PMID:20664735 NCBI chr 7:114,769,758...114,805,877
Ensembl chr 7:114,769,759...114,805,941 		JBrowse link
G Tff3 trefoil factor 3 decreases expression ISO gamma-Linolenic Acid results in decreased expression of TFF3 mRNA CTD PMID:20664735 NCBI chr20:9,194,623...9,199,333
Ensembl chr20:9,194,626...9,199,333 		JBrowse link
G Tjp1 tight junction protein 1 multiple interactions ISO [gamma-Linolenic Acid co-treated with Iodine co-treated with Selenium] results in increased expression of and results in increased localization of TJP1 protein CTD PMID:16514648 NCBI chr 1:128,260,330...128,505,018
Ensembl chr 1:128,260,330...128,505,158 		JBrowse link
G Tnf tumor necrosis factor decreases expression ISO gamma-Linolenic Acid results in decreased expression of TNF protein CTD PMID:9415022 NCBI chr20:3,626,685...3,629,303
Ensembl chr20:3,626,532...3,629,303 		JBrowse link
G Trpv1 transient receptor potential cation channel, subfamily V, member 1 multiple interactions EXP gamma-Linolenic Acid inhibits the reaction [Capsaicin results in increased activity of TRPV1 protein] CTD PMID:17038422 NCBI chr10:58,349,936...58,375,021
Ensembl chr10:58,340,223...58,375,021 		JBrowse link
G Txn1 thioredoxin 1 increases expression ISO gamma-Linolenic Acid results in increased expression of TXN mRNA CTD PMID:20664735 NCBI chr 5:77,507,455...77,519,685
Ensembl chr 5:77,507,321...77,520,307 		JBrowse link
G Txnrd1 thioredoxin reductase 1 increases expression ISO gamma-Linolenic Acid results in increased expression of TXNRD1 mRNA CTD PMID:20664735 NCBI chr 7:22,717,620...22,802,553
Ensembl chr 7:22,719,317...22,739,817 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 20874
    role 20844
      biological role 20831
        biochemical role 19888
          metabolite 19624
            eukaryotic metabolite 19368
              plant metabolite 16205
                gamma-linolenic acid 40
                  1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 20874
    subatomic particle 20883
      composite particle 20883
        hadron 20872
          baryon 20883
            nucleon 20872
              atomic nucleus 20883
                atom 20872
                  main group element atom 20796
                    p-block element atom 20796
                      carbon group element atom 20712
                        carbon atom 20706
                          organic molecular entity 20706
                            heteroorganic entity 20201
                              organochalcogen compound 19822
                                organooxygen compound 19713
                                  carbon oxoacid 17678
                                    carboxylic acid 17675
                                      monocarboxylic acid 17142
                                        fatty acid 14785
                                          unsaturated fatty acid 941
                                            polyunsaturated fatty acid 757
                                              trienoic fatty acid 265
                                                fatty acid 18:3 253
                                                  octadecatrienoic acid 253
                                                    linolenic acid 251
                                                      gamma-linolenic acid 40
                                                        1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
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