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ONTOLOGY REPORT - ANNOTATIONS


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 "Beilstein";   CAS:506-26-3 "KEGG COMPOUND";   CAS:506-26-3 "NIST Chemistry WebBook";   Drug_Central:1276 "DrugCentral";   HMDB:HMDB0003073;   KEGG:C06426;   KEGG:D07213;   KNApSAcK:C00001226;   LIPID_MAPS_instance:LMFA01030141 "LIPID MAPS"
 xref_mesh: MESH:D017965
 xref: MetaCyc:CPD-8117;   PMID:11385052 "Europe PMC";   PMID:24435467 "Europe PMC";   PMID:9732298 "Europe PMC";   Reaxys:1712253 "Reaxys";   Wikipedia:Gamma-Linolenic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:32391


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gamma-linolenic acid term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G Akr1c1 aldo-keto reductase family 1, member C1 JBrowse link 17 69,441,253 69,460,334 RGD:6480464
G Apoh apolipoprotein H JBrowse link 10 96,640,013 96,653,939 RGD:6480464
G Ar androgen receptor JBrowse link X 67,656,253 67,828,998 RGD:6480464
G Asah1 N-acylsphingosine amidohydrolase 1 JBrowse link 16 53,998,604 54,030,006 RGD:6480464
G Casp3 caspase 3 JBrowse link 16 48,845,011 48,863,249 RGD:6480464
G Ccna2 cyclin A2 JBrowse link 2 123,274,727 123,282,266 RGD:6480464
G Ccne1 cyclin E1 JBrowse link 1 94,485,830 94,495,112 RGD:6480464
G Cdk1 cyclin-dependent kinase 1 JBrowse link 20 20,576,341 20,591,510 RGD:6480464
G Cldn5 claudin 5 JBrowse link 11 86,356,292 86,357,718 RGD:6480464
G Clta clathrin, light chain A JBrowse link 5 59,490,689 59,509,139 RGD:6480464
G Fth1 ferritin heavy chain 1 JBrowse link 1 226,030,940 226,033,228 RGD:6480464
G Gclc glutamate-cysteine ligase, catalytic subunit JBrowse link 8 85,059,051 85,097,471 RGD:6480464
G Grk5 G protein-coupled receptor kinase 5 JBrowse link 1 282,265,371 282,467,842 RGD:6480464
G Hexb hexosaminidase subunit beta JBrowse link 2 27,983,925 28,003,260 RGD:6480464
G Hmox1 heme oxygenase 1 JBrowse link 19 14,508,634 14,515,455 RGD:6480464
G Il2 interleukin 2 JBrowse link 2 123,847,150 123,851,854 RGD:6480464
G Junb JunB proto-oncogene, AP-1 transcription factor subunit JBrowse link 19 26,092,972 26,094,756 RGD:6480464
G Kynu kynureninase JBrowse link 3 28,416,926 28,566,939 RGD:6480464
G LOC103690190 histone H2A type 1-E JBrowse link 17 44,747,686 44,748,229 RGD:6480464
G Mapk3 mitogen activated protein kinase 3 JBrowse link 1 198,192,773 198,198,975 RGD:6480464
G Mmp11 matrix metallopeptidase 11 JBrowse link 20 13,670,051 13,678,834 RGD:6480464
G Myc MYC proto-oncogene, bHLH transcription factor JBrowse link 7 102,586,313 102,591,240 RGD:6480464
G Ocln occludin JBrowse link 2 30,527,327 30,577,218 RGD:6480464
G Parp1 poly (ADP-ribose) polymerase 1 JBrowse link 13 98,857,255 98,889,444 RGD:6480464
G Pcna proliferating cell nuclear antigen JBrowse link 3 124,880,698 124,884,570 RGD:6480464
G Pdlim1 PDZ and LIM domain 1 JBrowse link 1 259,308,326 259,357,006 RGD:6480464
G Plin2 perilipin 2 JBrowse link 5 104,984,413 105,010,863 RGD:6480464
G Ppara peroxisome proliferator activated receptor alpha JBrowse link 7 126,618,872 126,687,282 RGD:6480464
G Pparg peroxisome proliferator-activated receptor gamma JBrowse link 4 147,274,055 147,399,383 RGD:6480464
G Ptgr1 prostaglandin reductase 1 JBrowse link 5 76,110,746 76,129,361 RGD:6480464
G Ptgs2 prostaglandin-endoperoxide synthase 2 JBrowse link 13 67,351,230 67,356,920 RGD:6480464
G Skp2 S-phase kinase associated protein 2 JBrowse link 2 58,506,146 58,534,211 RGD:6480464
G Slc3a2 solute carrier family 3 member 2 JBrowse link 1 224,906,566 224,921,029 RGD:6480464
G St13 ST13, Hsp70 interacting protein JBrowse link 7 122,585,770 122,635,731 RGD:6480464
G Tff3 trefoil factor 3 JBrowse link 20 9,850,800 9,855,481 RGD:6480464
G Tjp1 tight junction protein 1 JBrowse link 1 126,146,489 126,515,359 RGD:6480464
G Tnf tumor necrosis factor JBrowse link 20 5,189,382 5,192,000 RGD:6480464
G Trpv1 transient receptor potential cation channel, subfamily V, member 1 JBrowse link 10 59,799,123 59,824,208 RGD:6480464
G Txn1 thioredoxin 1 JBrowse link 5 75,049,735 75,057,731 RGD:6480464
G Txnrd1 thioredoxin reductase 1 JBrowse link 7 26,946,124 26,984,400 RGD:6480464

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19669
    role 19613
      biological role 19611
        biochemical role 19138
          metabolite 19106
            eukaryotic metabolite 18748
              plant metabolite 17044
                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 19669
    subatomic particle 19665
      composite particle 19665
        hadron 19665
          baryon 19665
            nucleon 19665
              atomic nucleus 19665
                atom 19665
                  main group element atom 19545
                    p-block element atom 19545
                      carbon group element atom 19428
                        carbon atom 19420
                          organic molecular entity 19420
                            organic group 18343
                              organic divalent group 18334
                                organodiyl group 18334
                                  carbonyl group 18222
                                    carbonyl compound 18222
                                      carboxylic acid 17923
                                        monocarboxylic acid 17256
                                          fatty acid 15814
                                            unsaturated fatty acid 888
                                              polyunsaturated fatty acid 646
                                                trienoic fatty acid 102
                                                  fatty acid 18:3 88
                                                    octadecatrienoic acid 88
                                                      linolenic acid 84
                                                        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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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.