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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, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.
Synonyms:exact_synonym: (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
 related_synonym: (6,9,12)-linolenic 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;   Formula=C18H30O2;   GLA;   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-;   InChIKey=VZCCETWTMQHEPK-QNEBEIHSSA-N;   Octadeca-6,9,12-triensaeure;   SMILES=CCCCC\\C=C/C\\C=C/C\\C=C/CCCCC(O)=O;   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;   Drug_Central:1276;   HMDB:HMDB0003073;   KEGG:C06426;   KEGG:D07213;   KNApSAcK:C00001226;   LIPID_MAPS_instance:LMFA01030141
 xref_mesh: MESH:D017965
 xref: MetaCyc:CPD-8117;   PMID:11385052;   PMID:24435467;   PMID:9732298;   Reaxys:1712253;   Wikipedia:Gamma-Linolenic_acid
 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 chr17:65,810,475...65,837,326 		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 chr10:93,310,977...93,356,329 		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:63,104,771...63,273,925 		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 chr16:50,966,229...51,008,233 		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 chr16:45,662,910...45,684,648 		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 2:119,426,089...119,433,577 		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 1:90,781,949...90,791,101 		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 chr20:19,266,248...19,281,408 		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 chr11:82,211,475...82,214,992 		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 5:58,245,442...58,263,472 		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 1:206,627,103...206,725,424 		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 8:78,630,127...78,668,544 		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 1:260,028,242...260,218,701 		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 2:28,484,012...28,504,223 		JBrowse link
G Hist1h2al1 histone cluster 1 H2A family like 1 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 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 chr19:13,467,244...13,474,079 		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 2:120,004,862...120,009,566 		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 chr19:23,176,294...23,178,035 		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 3:27,778,772...27,929,488 		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 1:181,366,637...181,372,863 		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 chr20:12,730,836...12,739,628 		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 7:93,593,705...93,598,630 		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 2:31,657,220...31,764,150 		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 chr13:92,307,586...92,339,404 		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 3:119,498,810...119,502,995 		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 1:239,042,385...239,091,076 		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 5:101,154,411...101,242,319 		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 7:116,832,756...116,895,346 		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 4:148,423,194...148,548,468 		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 5:73,784,009...73,802,666 		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 chr13:62,163,932...62,172,188 		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 2:58,161,229...58,189,338 		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 1:205,604,468...205,618,931 		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 7:112,844,375...112,925,945 		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 chr20:9,193,262...9,198,054 		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 1:118,849,838...119,094,432 		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 chr20:3,622,011...3,624,629 		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 chr10:57,851,428...57,876,513 		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 5:72,711,933...72,724,629 		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 7:20,830,045...20,907,863 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19887
    role 19858
      biological role 19856
        biochemical role 19566
          metabolite 19554
            eukaryotic metabolite 19381
              plant metabolite 18021
                gamma-linolenic acid 40
                  1-(gamma-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate 0
                  1-(gamma-linolenoyl)-sn-glycero-3-phosphate 0
                  1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine 0
                  1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine 0
                  1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                  1-hexadecyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                  1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                  1-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                  1-tetracosyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                  10(R)-HPO(6,8,12)TrE 0
                  10-HPO(6,8,12)TrE + 0
                  cholesteryl gamma-linolenate 0
                  gamma-linolenoyl bioconjugate + 0
                  gamma-linolenoyl group 0
                  gamma-linolenoyl-CoA 0
                  gamma-linolenoyl-containing glycerolipid + 0
                  methyl gamma-linolenate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19887
    subatomic particle 19885
      composite particle 19885
        hadron 19885
          baryon 19885
            nucleon 19885
              atomic nucleus 19885
                atom 19885
                  main group element atom 19824
                    p-block element atom 19824
                      carbon group element atom 19763
                        carbon atom 19760
                          organic molecular entity 19760
                            heteroorganic entity 19521
                              organochalcogen compound 19282
                                organooxygen compound 19197
                                  carbon oxoacid 18676
                                    carboxylic acid 18673
                                      monocarboxylic acid 18012
                                        fatty acid 16849
                                          unsaturated fatty acid 1692
                                            polyunsaturated fatty acid 847
                                              trienoic fatty acid 268
                                                fatty acid 18:3 256
                                                  octadecatrienoic acid 256
                                                    linolenic acid 254
                                                      gamma-linolenic acid 40
                                                        1-(gamma-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate 0
                                                        1-(gamma-linolenoyl)-sn-glycero-3-phosphate 0
                                                        1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine 0
                                                        1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine 0
                                                        1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                        1-hexadecyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                        1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                        1-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                        1-tetracosyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                        10(R)-HPO(6,8,12)TrE 0
                                                        10-HPO(6,8,12)TrE + 0
                                                        cholesteryl gamma-linolenate 0
                                                        gamma-linolenoyl bioconjugate + 0
                                                        gamma-linolenoyl group 0
                                                        gamma-linolenoyl-CoA 0
                                                        gamma-linolenoyl-containing glycerolipid + 0
                                                        methyl gamma-linolenate 0
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