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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 EXP gamma-Linolenic Acid results in increased expression of AKR1C1 mRNA CTD PMID:20664735 NCBI chr10:4,963,415...4,983,283
Ensembl chr10:4,963,253...4,983,283
JBrowse link
G AKR1C4 aldo-keto reductase family 1 member C4 increases expression EXP gamma-Linolenic Acid results in increased expression of AKR1C4 mRNA CTD PMID:20664735 NCBI chr10:5,196,837...5,218,949
Ensembl chr10:5,195,462...5,218,949
JBrowse link
G APOH apolipoprotein H decreases expression EXP gamma-Linolenic Acid results in decreased expression of APOH mRNA CTD PMID:20664735 NCBI chr17:66,212,033...66,229,415
Ensembl chr17:66,212,033...66,256,525
JBrowse link
G AR androgen receptor multiple interactions EXP gamma-Linolenic Acid inhibits the reaction [Metribolone results in increased activity of AR protein] CTD PMID:18324785 NCBI chr  X:67,544,021...67,730,619
Ensembl chr  X:67,544,021...67,730,619
JBrowse link
G ASAH1 N-acylsphingosine amidohydrolase 1 increases expression EXP gamma-Linolenic Acid results in increased expression of ASAH1 mRNA CTD PMID:20664735 NCBI chr 8:18,055,992...18,084,961
Ensembl chr 8:18,055,992...18,084,998
JBrowse link
G CASP3 caspase 3 increases activity EXP gamma-Linolenic Acid results in increased activity of CASP3 protein CTD PMID:16857180 NCBI chr 4:184,627,696...184,649,447
Ensembl chr 4:184,627,696...184,649,509
JBrowse link
G CCNA2 cyclin A2 decreases expression EXP gamma-Linolenic Acid results in decreased expression of CCNA2 protein CTD PMID:15318936 NCBI chr 4:121,816,444...121,823,883
Ensembl chr 4:121,816,444...121,823,883
Ensembl chr 4:121,816,444...121,823,883
JBrowse link
G CCNE1 cyclin E1 decreases expression EXP gamma-Linolenic Acid results in decreased expression of CCNE1 protein CTD PMID:15318936 NCBI chr19:29,811,991...29,824,312
Ensembl chr19:29,811,991...29,824,312
JBrowse link
G CDK1 cyclin dependent kinase 1 decreases expression EXP gamma-Linolenic Acid results in decreased expression of CDK1 protein CTD PMID:15318936 NCBI chr10:60,778,331...60,794,852
Ensembl chr10:60,778,331...60,794,852
JBrowse link
G CLDN5 claudin 5 multiple interactions EXP [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 chr22:19,523,024...19,525,337
Ensembl chr22:19,523,024...19,527,545
JBrowse link
G CLTA clathrin light chain A increases expression EXP gamma-Linolenic Acid results in increased expression of CLTA mRNA CTD PMID:20664735 NCBI chr 9:36,190,855...36,212,059
Ensembl chr 9:36,190,856...36,304,781
JBrowse link
G FTH1 ferritin heavy chain 1 increases expression EXP gamma-Linolenic Acid results in increased expression of FTH1 mRNA CTD PMID:20664735 NCBI chr11:61,964,285...61,967,634
Ensembl chr11:61,959,718...61,967,634
JBrowse link
G GCLC glutamate-cysteine ligase catalytic subunit increases activity
increases expression
EXP 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 6:53,497,341...53,545,101
Ensembl chr 6:53,497,341...53,616,970
JBrowse link
G GRK5 G protein-coupled receptor kinase 5 increases expression EXP gamma-Linolenic Acid results in increased expression of GRK5 mRNA CTD PMID:20664735 NCBI chr10:119,207,571...119,459,745
Ensembl chr10:119,207,571...119,459,745
JBrowse link
G H2AC6 H2A clustered histone 6 decreases expression EXP gamma-Linolenic Acid results in decreased expression of H2AC6 mRNA CTD PMID:20664735 NCBI chr 6:26,124,172...26,124,690
Ensembl chr 6:26,124,145...26,139,116
JBrowse link
G HEXB hexosaminidase subunit beta increases expression EXP gamma-Linolenic Acid results in increased expression of HEXB mRNA CTD PMID:20664735 NCBI chr 5:74,640,023...74,721,288
Ensembl chr 5:74,640,023...74,722,647
JBrowse link
G HMOX1 heme oxygenase 1 increases expression EXP 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 chr22:35,381,096...35,394,207
Ensembl chr22:35,380,361...35,394,207
JBrowse link
G IL2 interleukin 2 affects expression EXP gamma-Linolenic Acid affects the expression of IL2 protein CTD PMID:9415022 NCBI chr 4:122,451,470...122,456,725
Ensembl chr 4:122,451,470...122,456,725
JBrowse link
G JUNB JunB proto-oncogene, AP-1 transcription factor subunit decreases expression EXP gamma-Linolenic Acid results in decreased expression of JUNB protein CTD PMID:15318936 NCBI chr19:12,791,486...12,793,315
Ensembl chr19:12,791,486...12,793,315
JBrowse link
G KYNU kynureninase decreases expression EXP gamma-Linolenic Acid results in decreased expression of KYNU mRNA CTD PMID:20664735 NCBI chr 2:142,877,664...143,055,833
Ensembl chr 2:142,877,657...143,055,833
JBrowse link
G MAPK3 mitogen-activated protein kinase 3 decreases expression EXP gamma-Linolenic Acid results in decreased expression of MAPK3 protein CTD PMID:15318936 NCBI chr16:30,114,105...30,123,309
Ensembl chr16:30,114,105...30,123,506
JBrowse link
G MMP11 matrix metallopeptidase 11 decreases expression EXP gamma-Linolenic Acid results in decreased expression of MMP11 mRNA CTD PMID:20664735 NCBI chr22:23,772,849...23,784,316
Ensembl chr22:23,768,226...23,784,316
JBrowse link
G MT1G metallothionein 1G increases expression EXP gamma-Linolenic Acid results in increased expression of MT1G mRNA CTD PMID:20664735 NCBI chr16:56,666,730...56,668,065
Ensembl chr16:56,666,731...56,668,065
Ensembl chr16:56,666,731...56,668,065
JBrowse link
G MT1L metallothionein 1L, pseudogene increases expression EXP gamma-Linolenic Acid results in increased expression of MT1L mRNA CTD PMID:20664735 NCBI chr16:56,617,461...56,618,818
Ensembl chr16:56,617,476...56,618,818
JBrowse link
G MYC MYC proto-oncogene, bHLH transcription factor decreases expression EXP gamma-Linolenic Acid results in decreased expression of MYC protein CTD PMID:15318936 NCBI chr 8:127,735,434...127,742,951
Ensembl chr 8:127,735,434...127,742,951
JBrowse link
G OCLN occludin multiple interactions EXP [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 5:69,492,547...69,558,104
Ensembl chr 5:69,492,292...69,558,104
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 chr 1:226,360,691...226,408,093
Ensembl chr 1:226,360,691...226,408,093
JBrowse link
G PCNA proliferating cell nuclear antigen decreases expression EXP gamma-Linolenic Acid results in decreased expression of PCNA mRNA CTD PMID:20664735 NCBI chr20:5,114,953...5,126,622
Ensembl chr20:5,114,953...5,126,626
JBrowse link
G PDLIM1 PDZ and LIM domain 1 decreases expression EXP gamma-Linolenic Acid results in decreased expression of PDLIM1 mRNA CTD PMID:20664735 NCBI chr10:95,237,569...95,291,006
Ensembl chr10:95,237,572...95,291,012
JBrowse link
G PLIN2 perilipin 2 increases expression EXP gamma-Linolenic Acid results in increased expression of PLIN2 mRNA CTD PMID:20664735 NCBI chr 9:19,108,391...19,127,518
Ensembl chr 9:19,108,375...19,149,290
JBrowse link
G PPARA peroxisome proliferator activated receptor alpha multiple interactions EXP gamma-Linolenic Acid binds to and results in increased activity of PPARA protein CTD PMID:10403814 NCBI chr22:46,150,526...46,243,756
Ensembl chr22:46,150,521...46,243,756
JBrowse link
G PPARG peroxisome proliferator activated receptor gamma multiple interactions EXP gamma-Linolenic Acid binds to and results in increased activity of PPARG protein CTD PMID:15318936 NCBI chr 3:12,287,368...12,434,344
Ensembl chr 3:12,287,368...12,434,356
JBrowse link
G PTGR1 prostaglandin reductase 1 increases expression EXP gamma-Linolenic Acid results in increased expression of PTGR1 mRNA CTD PMID:20664735 NCBI chr 9:111,549,722...111,599,855
Ensembl chr 9:111,549,722...111,599,893
JBrowse link
G PTGS2 prostaglandin-endoperoxide synthase 2 increases expression EXP gamma-Linolenic Acid results in increased expression of PTGS2 mRNA CTD PMID:17092368 NCBI chr 1:186,671,791...186,680,423
Ensembl chr 1:186,671,791...186,680,423
JBrowse link
G S100P S100 calcium binding protein P increases expression EXP gamma-Linolenic Acid results in increased expression of S100P mRNA CTD PMID:20664735 NCBI chr 4:6,693,878...6,697,170
Ensembl chr 4:6,693,878...6,697,170
JBrowse link
G SKP2 S-phase kinase associated protein 2 decreases expression EXP gamma-Linolenic Acid results in decreased expression of SKP2 mRNA CTD PMID:20664735 NCBI chr 5:36,152,067...36,184,319
Ensembl chr 5:36,151,989...36,184,319
JBrowse link
G SLC3A2 solute carrier family 3 member 2 increases expression EXP gamma-Linolenic Acid results in increased expression of SLC3A2 mRNA CTD PMID:20664735 NCBI chr11:62,856,109...62,888,860
Ensembl chr11:62,856,102...62,888,875
JBrowse link
G ST13 ST13 Hsp70 interacting protein increases expression EXP gamma-Linolenic Acid results in increased expression of ST13 mRNA CTD PMID:20664735 NCBI chr22:40,824,535...40,856,639
Ensembl chr22:40,824,535...40,856,639
JBrowse link
G TFF3 trefoil factor 3 decreases expression EXP gamma-Linolenic Acid results in decreased expression of TFF3 mRNA CTD PMID:20664735 NCBI chr21:42,311,667...42,315,409
Ensembl chr21:42,311,667...42,315,651
JBrowse link
G TJP1 tight junction protein 1 multiple interactions EXP [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 chr15:29,699,367...29,969,049
Ensembl chr15:29,699,367...29,968,865
JBrowse link
G TNF tumor necrosis factor decreases expression EXP gamma-Linolenic Acid results in decreased expression of TNF protein CTD PMID:9415022 NCBI chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336
JBrowse link
G TRPV1 transient receptor potential cation channel subfamily V member 1 multiple interactions ISO gamma-Linolenic Acid inhibits the reaction [Capsaicin results in increased activity of TRPV1 protein] CTD PMID:17038422 NCBI chr17:3,565,446...3,609,411
Ensembl chr17:3,565,444...3,609,411
JBrowse link
G TXN thioredoxin increases expression EXP gamma-Linolenic Acid results in increased expression of TXN mRNA CTD PMID:20664735 NCBI chr 9:110,243,810...110,256,507
Ensembl chr 9:110,243,810...110,256,507
JBrowse link
G TXNRD1 thioredoxin reductase 1 increases expression EXP gamma-Linolenic Acid results in increased expression of TXNRD1 mRNA CTD PMID:20664735 NCBI chr12:104,215,779...104,350,307
Ensembl chr12:104,215,779...104,350,307
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 24161
    role 24056
      biological role 24022
        biochemical role 23294
          metabolite 23198
            eukaryotic metabolite 22870
              plant metabolite 19767
                gamma-linolenic acid 44
                  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 24161
    subatomic particle 24116
      composite particle 24116
        hadron 24116
          baryon 24116
            nucleon 24116
              atomic nucleus 24116
                atom 24116
                  main group element atom 23948
                    p-block element atom 23948
                      carbon group element atom 23681
                        carbon atom 23637
                          organic molecular entity 23637
                            organic group 22153
                              organic divalent group 22127
                                organodiyl group 22127
                                  carbonyl group 22106
                                    carbonyl compound 22106
                                      carboxylic acid 21136
                                        monocarboxylic acid 20004
                                          fatty acid 18139
                                            unsaturated fatty acid 931
                                              polyunsaturated fatty acid 679
                                                trienoic fatty acid 111
                                                  fatty acid 18:3 97
                                                    octadecatrienoic acid 97
                                                      linolenic acid 93
                                                        gamma-linolenic acid 44
                                                          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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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.