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ONTOLOGY REPORT - ANNOTATIONS


Term:alpha-linolenic acid
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Accession:CHEBI:27432 term browser browse the term
Definition:A linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect.
Synonyms:exact_synonym: (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
 related_synonym: (9,12,15)-linolenic acid;   (9Z,12Z,15Z)-Octadecatrienoic acid;   (Z,Z,Z)-9,12,15-octadecatrienoic acid;   9,12,15-Octadecatrienoic acid;   ALA;   Formula=C18H30O2;   InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-;   InChIKey=DTOSIQBPPRVQHS-PDBXOOCHSA-N;   SMILES=CC\\C=C/C\\C=C/C\\C=C/CCCCCCCC(O)=O;   all-cis-9,12,15-octadecatrienoic acid;   cis,cis,cis-9,12,15-octadecatrienoic acid;   cis-Delta(9,12,15)-octadecatrienoic acid;   linolenic acid
 alt_id: CHEBI:10298;   CHEBI:22462;   CHEBI:43891
 xref: Beilstein:1727693 "Beilstein";   CAS:463-40-1 "ChemIDplus";   CAS:463-40-1 "KEGG COMPOUND";   CAS:463-40-1 "NIST Chemistry WebBook";   DrugBank:DB00132;   Drug_Central:4618 "DrugCentral";   Gmelin:57558 "Gmelin";   HMDB:HMDB0001388;   KEGG:C06427;   KNApSAcK:C00007247;   LIPID_MAPS_instance:LMFA01030152 "LIPID MAPS"
 xref_mesh: MESH:D017962
 xref: MetaCyc:LINOLENIC_ACID;   PDBeChem:LNL;   PMID:10232625 "Europe PMC";   PMID:11304127 "Europe PMC";   PMID:19269799 "Europe PMC";   PMID:24320056 "Europe PMC";   PMID:24639012 "Europe PMC";   PMID:24855655 "Europe PMC";   Reaxys:1727693 "Reaxys";   Wikipedia:Alpha-Linolenic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:32387;   is_conjugate_acid_of CHEBI:528881


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alpha-linolenic acid term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G ABCB11 ATP binding cassette subfamily B member 11 JBrowse link 2 168,915,468 169,031,396 RGD:6480464
G ACACA acetyl-CoA carboxylase alpha JBrowse link 17 37,084,992 37,406,836 RGD:6480464
G ACLY ATP citrate lyase JBrowse link 17 41,866,916 41,930,542 RGD:6480464
G BCHE butyrylcholinesterase JBrowse link 3 165,772,904 165,837,451 RGD:6480464
G CAT catalase JBrowse link 11 34,438,934 34,472,060 RGD:6480464
G CEBPB CCAAT enhancer binding protein beta JBrowse link 20 50,190,583 50,192,690 RGD:6480464
G CPT1A carnitine palmitoyltransferase 1A JBrowse link 11 68,754,620 68,844,410 RGD:6480464
G CYBB cytochrome b-245 beta chain JBrowse link X 37,780,059 37,813,461 RGD:6480464
G CYP1A2 cytochrome P450 family 1 subfamily A member 2 JBrowse link 15 74,748,845 74,756,607 RGD:6480464
G CYP24A1 cytochrome P450 family 24 subfamily A member 1 JBrowse link 20 54,145,731 54,174,032 RGD:6480464
G CYP2A6 cytochrome P450 family 2 subfamily A member 6 JBrowse link 19 40,843,541 40,850,447 RGD:6480464
G CYP2C19 cytochrome P450 family 2 subfamily C member 19 JBrowse link 10 94,762,681 94,855,547 RGD:6480464
G CYP2C9 cytochrome P450 family 2 subfamily C member 9 JBrowse link 10 94,938,658 94,990,091 RGD:6480464
G CYP2E1 cytochrome P450 family 2 subfamily E member 1 JBrowse link 10 133,527,363 133,539,123 RGD:6480464
G CYP3A4 cytochrome P450 family 3 subfamily A member 4 JBrowse link 7 99,756,967 99,784,184 RGD:6480464
G DIO1 iodothyronine deiodinase 1 JBrowse link 1 53,894,187 53,911,086 RGD:6480464
G DIO2 iodothyronine deiodinase 2 JBrowse link 14 80,197,526 80,231,057 RGD:6480464
G DIO3 iodothyronine deiodinase 3 JBrowse link 14 101,561,351 101,563,452 RGD:6480464
G FADS1 fatty acid desaturase 1 JBrowse link 11 61,799,627 61,817,003 RGD:6480464
G FASN fatty acid synthase JBrowse link 17 82,078,338 82,098,303 RGD:6480464
G GCLC glutamate-cysteine ligase catalytic subunit JBrowse link 6 53,497,341 53,545,101 RGD:6480464
G GPT glutamic--pyruvic transaminase JBrowse link 8 144,502,217 144,507,174 RGD:6480464
G GSTA1 glutathione S-transferase alpha 1 JBrowse link 6 52,791,371 52,803,827 RGD:6480464
G HMOX1 heme oxygenase 1 JBrowse link 22 35,381,096 35,394,207 RGD:6480464
G IFNG interferon gamma JBrowse link 12 68,154,768 68,159,740 RGD:6480464
G IL1B interleukin 1 beta JBrowse link 2 112,829,751 112,836,843 RGD:6480464
G IL4 interleukin 4 JBrowse link 5 132,673,986 132,682,678 RGD:6480464
G IL6 interleukin 6 JBrowse link 7 22,725,889 22,732,002 RGD:6480464
G KNG1 kininogen 1 JBrowse link 3 186,717,359 186,744,410 RGD:6480464
G NFE2L2 nuclear factor, erythroid 2 like 2 JBrowse link 2 177,230,303 177,265,131 RGD:6480464
G NQO1 NAD(P)H quinone dehydrogenase 1 JBrowse link 16 69,709,401 69,726,560 RGD:6480464
G NR1H2 nuclear receptor subfamily 1 group H member 2 JBrowse link 19 50,376,457 50,383,388 RGD:6480464
G NR1H4 nuclear receptor subfamily 1 group H member 4 JBrowse link 12 100,473,866 100,564,414 RGD:6480464
G PCK1 phosphoenolpyruvate carboxykinase 1 JBrowse link 20 57,561,110 57,568,121 RGD:6480464
G PLIN2 perilipin 2 JBrowse link 9 19,108,391 19,127,606 RGD:6480464
G PPARA peroxisome proliferator activated receptor alpha JBrowse link 22 46,150,526 46,243,756 RGD:6480464
G PPARD peroxisome proliferator activated receptor delta JBrowse link 6 35,342,558 35,428,191 RGD:6480464
G PPARG peroxisome proliferator activated receptor gamma JBrowse link 3 12,287,485 12,434,356 RGD:6480464
G PTGS2 prostaglandin-endoperoxide synthase 2 JBrowse link 1 186,671,791 186,680,423 RGD:6480464
G RXRA retinoid X receptor alpha JBrowse link 9 134,326,455 134,440,586 RGD:6480464
G SREBF1 sterol regulatory element binding transcription factor 1 JBrowse link 17 17,811,334 17,837,017 RGD:6480464
G TNF tumor necrosis factor JBrowse link 6 31,575,565 31,578,336 RGD:6480464
G TRPV1 transient receptor potential cation channel subfamily V member 1 JBrowse link 17 3,565,446 3,609,411 RGD:6480464
G UCP2 uncoupling protein 2 JBrowse link 11 73,974,671 73,982,872 RGD:6480464
G VDR vitamin D receptor JBrowse link 12 47,841,537 47,905,031 RGD:6480464
1,2,3-trilinolenoylglycerol term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G ABCA1 ATP binding cassette subfamily A member 1 JBrowse link 9 104,781,006 104,928,232 RGD:6480464
G ABCG5 ATP binding cassette subfamily G member 5 JBrowse link 2 43,806,154 43,838,840 RGD:6480464
G ABCG8 ATP binding cassette subfamily G member 8 JBrowse link 2 43,831,942 43,882,988 RGD:6480464
G CYP27A1 cytochrome P450 family 27 subfamily A member 1 JBrowse link 2 218,781,733 218,815,293 RGD:6480464
G HMGCR 3-hydroxy-3-methylglutaryl-CoA reductase JBrowse link 5 75,336,334 75,362,116 RGD:6480464
G MTTP microsomal triglyceride transfer protein JBrowse link 4 99,564,078 99,623,997 RGD:6480464
G NPC1L1 NPC1 like intracellular cholesterol transporter 1 JBrowse link 7 44,512,440 44,541,651 RGD:6480464
cholesteryl linolenate term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G LIPC lipase C, hepatic type JBrowse link 15 58,410,457 58,569,844 RGD:6480464
G LIPG lipase G, endothelial type JBrowse link 18 49,560,699 49,599,185 RGD:6480464

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 23677
    role 23565
      application 22946
        pharmaceutical 22484
          drug 22484
            nutraceutical 9796
              alpha-linolenic acid 54
                (9Z,11R,12Z,15Z)-11-hydroperoxyoctadecatrienoic acid 0
                (9Z,11S,12Z,15Z)-11-hydroperoxyoctadecatrienoic acid 0
                (9Z,12Z,15Z)-octadecatrienamide 0
                (R)-2-hydroperoxy-alpha-linolenic acid 0
                (R)-2-hydroxy-alpha-linolenic acid 0
                1,2,3-trilinolenoylglycerol 7
                1,2-di-(alpha-linolenoyl)-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol 0
                1,2-di-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                1,3-dilinolenoylglycerol 0
                1-(9Z,12Z,15Z)-octadecatrienoyl-2-(7Z,10Z,13Z)-hexadecatrienoyl-3-(beta-D-galactosyl)-sn-glycerol 0
                1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol 0
                1-[(9Z)-octadecenoyl]-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                1-[(9Z,12Z,15Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine 0
                1-alpha-linolenoyl-2-[(11Z)-icosenoyl]-sn-glycerol 0
                1-alpha-linolenoyl-2-[(11Z,14Z)-icosadienoyl]-sn-glycerol 0
                1-alpha-linolenoyl-2-[(5Z,8Z,11Z)-icosatrienoyl]-sn-glycerol 0
                1-alpha-linolenoyl-2-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycerol 0
                1-alpha-linolenoyl-2-hexadecanoylphosphatidylglycerol 0
                1-alpha-linolenoyl-2-icosanoyl-sn-glycerol 0
                1-alpha-linolenoyl-2-oleoylglycerol + 0
                1-alpha-linolenoylglycerol + 0
                1-heptadecanoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                1-linolenoyl-2-oleoyl-sn-glycero-3-phosphate 0
                1-linolenoyl-sn-glycero-3-phosphate 0
                1-linolenyl-2-linoleyl-PAP 0
                1-oleoyl-2-(alpha-linolenoyl)-sn-glycerol 0
                1-oleoyl-2-linolenoyl-PAP 0
                1-palmitoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                1-stearoyl-2-(alpha-linolenoyl)-sn-glycero-3-phosphocholine 0
                1-tetradecanoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                2,3-dilinolenoyl-sn-glycerol 0
                2-alpha-linolenoylglycerol 0
                N-(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl-(2S)-hydroxyglycine 0
                N-(9Z,12Z,15Z)-octadecatrienoylglycine 0
                alpha-linolenoyl bioconjugate + 0
                alpha-linolenoyl group 0
                alpha-linolenoyl-CoA 0
                alpha-linolenoyl-containing glycerolipid + 0
                alpha-linolenoyl-sn-glycero-3-phosphocholine + 0
                cholesteryl linolenate 2
                ethyl linolenate 0
                linolenic acid anilide 0
                methyl linolenate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 23677
    subatomic particle 23624
      composite particle 23624
        hadron 23624
          baryon 23624
            nucleon 23624
              atomic nucleus 23624
                atom 23624
                  main group element atom 23441
                    p-block element atom 23441
                      carbon group element atom 23142
                        carbon atom 23118
                          organic molecular entity 23118
                            organic group 21814
                              organic divalent group 21784
                                organodiyl group 21784
                                  carbonyl group 21756
                                    carbonyl compound 21756
                                      carboxylic acid 20776
                                        monocarboxylic acid 19753
                                          fatty acid 18115
                                            unsaturated fatty acid 910
                                              polyunsaturated fatty acid 662
                                                trienoic fatty acid 108
                                                  fatty acid 18:3 94
                                                    octadecatrienoic acid 94
                                                      linolenic acid 90
                                                        alpha-linolenic acid 54
                                                          (9Z,11R,12Z,15Z)-11-hydroperoxyoctadecatrienoic acid 0
                                                          (9Z,11S,12Z,15Z)-11-hydroperoxyoctadecatrienoic acid 0
                                                          (9Z,12Z,15Z)-octadecatrienamide 0
                                                          (R)-2-hydroperoxy-alpha-linolenic acid 0
                                                          (R)-2-hydroxy-alpha-linolenic acid 0
                                                          1,2,3-trilinolenoylglycerol 7
                                                          1,2-di-(alpha-linolenoyl)-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol 0
                                                          1,2-di-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                          1,3-dilinolenoylglycerol 0
                                                          1-(9Z,12Z,15Z)-octadecatrienoyl-2-(7Z,10Z,13Z)-hexadecatrienoyl-3-(beta-D-galactosyl)-sn-glycerol 0
                                                          1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol 0
                                                          1-[(9Z)-octadecenoyl]-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                          1-[(9Z,12Z,15Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine 0
                                                          1-alpha-linolenoyl-2-[(11Z)-icosenoyl]-sn-glycerol 0
                                                          1-alpha-linolenoyl-2-[(11Z,14Z)-icosadienoyl]-sn-glycerol 0
                                                          1-alpha-linolenoyl-2-[(5Z,8Z,11Z)-icosatrienoyl]-sn-glycerol 0
                                                          1-alpha-linolenoyl-2-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycerol 0
                                                          1-alpha-linolenoyl-2-hexadecanoylphosphatidylglycerol 0
                                                          1-alpha-linolenoyl-2-icosanoyl-sn-glycerol 0
                                                          1-alpha-linolenoyl-2-oleoylglycerol + 0
                                                          1-alpha-linolenoylglycerol + 0
                                                          1-heptadecanoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                          1-linolenoyl-2-oleoyl-sn-glycero-3-phosphate 0
                                                          1-linolenoyl-sn-glycero-3-phosphate 0
                                                          1-linolenyl-2-linoleyl-PAP 0
                                                          1-oleoyl-2-(alpha-linolenoyl)-sn-glycerol 0
                                                          1-oleoyl-2-linolenoyl-PAP 0
                                                          1-palmitoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                          1-stearoyl-2-(alpha-linolenoyl)-sn-glycero-3-phosphocholine 0
                                                          1-tetradecanoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine 0
                                                          2,3-dilinolenoyl-sn-glycerol 0
                                                          2-alpha-linolenoylglycerol 0
                                                          N-(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl-(2S)-hydroxyglycine 0
                                                          N-(9Z,12Z,15Z)-octadecatrienoylglycine 0
                                                          alpha-linolenoyl bioconjugate + 0
                                                          alpha-linolenoyl group 0
                                                          alpha-linolenoyl-CoA 0
                                                          alpha-linolenoyl-containing glycerolipid + 0
                                                          alpha-linolenoyl-sn-glycero-3-phosphocholine + 0
                                                          cholesteryl linolenate 2
                                                          ethyl linolenate 0
                                                          linolenic acid anilide 0
                                                          methyl linolenate 0
paths to the root

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.