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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: Beilstein:1712253;   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 AKR1C4 mRNA CTD PMID:20664735 NCBI chr17:69,441,253...69,460,334
Ensembl chr17:69,441,223...69,460,321
JBrowse link
G Apoh apolipoprotein H decreases expression ISO gamma-Linolenic Acid results in decreased expression of APOH mRNA CTD PMID:20664735 NCBI chr10:96,640,013...96,653,939
Ensembl chr10:96,639,924...96,653,938
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:67,656,253...67,828,998
Ensembl chr  X:67,656,253...67,829,026
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 chr16:53,998,604...54,030,006
Ensembl chr16:53,998,560...54,040,836
JBrowse link
G Casp3 caspase 3 increases activity ISO gamma-Linolenic Acid results in increased activity of CASP3 protein CTD PMID:16857180 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ccna2 cyclin A2 decreases expression ISO gamma-Linolenic Acid results in decreased expression of CCNA2 protein CTD PMID:15318936 NCBI chr 2:123,274,727...123,282,266
Ensembl chr 2:123,275,881...123,282,214
JBrowse link
G Ccne1 cyclin E1 decreases expression ISO gamma-Linolenic Acid results in decreased expression of CCNE1 protein CTD PMID:15318936 NCBI chr 1:94,485,830...94,495,112
Ensembl chr 1:94,485,832...94,494,980
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 chr20:20,576,341...20,591,510
Ensembl chr20:20,576,377...20,591,549
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 chr11:86,356,292...86,357,718
Ensembl chr11:86,356,294...86,357,718
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 5:59,490,689...59,509,139
Ensembl chr 5:59,491,096...59,509,138
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 1:226,030,940...226,033,228
Ensembl chr 1:226,030,938...226,033,228
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 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
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 1:282,265,371...282,467,842
Ensembl chr 1:282,265,370...282,462,605
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 2:27,983,925...28,003,260
Ensembl chr 2:27,984,117...28,003,186
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 chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Il2 interleukin 2 affects expression ISO gamma-Linolenic Acid affects the expression of IL2 protein CTD PMID:9415022 NCBI chr 2:123,847,150...123,851,854
Ensembl chr 2:123,847,150...123,851,854
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 chr19:26,092,972...26,094,756
Ensembl chr19:26,092,974...26,094,756
JBrowse link
G Kynu kynureninase decreases expression ISO gamma-Linolenic Acid results in decreased expression of KYNU mRNA CTD PMID:20664735 NCBI chr 3:28,416,926...28,566,939
Ensembl chr 3:28,416,954...28,566,928
JBrowse link
G LOC103690190 histone H2A type 1-E decreases expression ISO gamma-Linolenic Acid results in decreased expression of H2AC6 mRNA CTD PMID:20664735 NCBI chr17:44,747,686...44,748,229
Ensembl chr17:44,747,796...44,748,188
Ensembl chr17:44,747,796...44,748,188
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mmp11 matrix metallopeptidase 11 decreases expression ISO gamma-Linolenic Acid results in decreased expression of MMP11 mRNA CTD PMID:20664735 NCBI chr20:13,670,051...13,678,834
Ensembl chr20:13,670,066...13,678,089
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 7:102,586,313...102,591,240
Ensembl chr 7:102,586,313...102,591,240
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 2:30,527,327...30,577,218
Ensembl chr 2:30,527,715...30,577,218
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 chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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 3:124,880,698...124,884,570
Ensembl chr 3:124,880,698...124,884,570
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 1:259,308,326...259,357,006
Ensembl chr 1:259,308,296...259,357,056
JBrowse link
G Plin2 perilipin 2 increases expression ISO gamma-Linolenic Acid results in increased expression of PLIN2 mRNA CTD PMID:20664735 NCBI chr 5:104,984,413...105,010,863
Ensembl chr 5:104,984,414...105,010,857
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 7:126,618,872...126,687,282
Ensembl chr 7:126,619,196...126,681,752
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 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
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 5:76,110,746...76,129,361
Ensembl chr 5:76,110,738...76,129,441
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 chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
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 2:58,506,146...58,534,211
Ensembl chr 2:58,506,151...58,534,211
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 1:224,906,566...224,921,029
Ensembl chr 1:224,906,554...224,921,092
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 7:122,585,770...122,635,731
Ensembl chr 7:122,585,771...122,635,731
JBrowse link
G Tff3 trefoil factor 3 decreases expression ISO gamma-Linolenic Acid results in decreased expression of TFF3 mRNA CTD PMID:20664735 NCBI chr20:9,850,800...9,855,481
Ensembl chr20:9,850,803...9,855,481
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 1:126,146,489...126,515,359
Ensembl chr 1:126,146,489...126,227,469
JBrowse link
G Tnf tumor necrosis factor decreases expression ISO gamma-Linolenic Acid results in decreased expression of TNF protein CTD PMID:9415022 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
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 chr10:59,799,123...59,824,208
Ensembl chr10:59,799,123...59,824,679
JBrowse link
G Txn1 thioredoxin 1 increases expression ISO gamma-Linolenic Acid results in increased expression of TXN mRNA CTD PMID:20664735 NCBI chr 5:75,049,735...75,057,731
Ensembl chr 5:75,049,747...75,057,752
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 7:26,946,124...26,984,400
Ensembl chr 7:26,946,125...26,984,400
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      biological role 19734
        biochemical role 19282
          metabolite 19263
            eukaryotic metabolite 18908
              plant metabolite 17360
                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 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    p-block element atom 19672
                      carbon group element atom 19574
                        carbon atom 19563
                          organic molecular entity 19563
                            organic group 18495
                              organic divalent group 18488
                                organodiyl group 18488
                                  carbonyl group 18391
                                    carbonyl compound 18391
                                      carboxylic acid 18061
                                        monocarboxylic acid 17407
                                          fatty acid 15845
                                            unsaturated fatty acid 922
                                              polyunsaturated fatty acid 663
                                                trienoic fatty acid 105
                                                  fatty acid 18:3 91
                                                    octadecatrienoic acid 91
                                                      linolenic acid 87
                                                        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
paths to the root

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