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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 3 55,480,024 55,587,946 RGD:6480464
G Acaca acetyl-CoA carboxylase alpha JBrowse link 10 71,519,392 71,719,910 RGD:6480464
G Acly ATP citrate lyase JBrowse link 10 88,392,248 88,442,845 RGD:6480464
G Bche butyrylcholinesterase JBrowse link 2 171,104,476 171,196,186 RGD:6480464
G Cat catalase JBrowse link 3 93,379,872 93,412,058 RGD:6480464
G Cebpb CCAAT/enhancer binding protein beta JBrowse link 3 164,424,502 164,425,933 RGD:6480464
G Cpt1a carnitine palmitoyltransferase 1A JBrowse link 1 218,568,157 218,629,679 RGD:6480464
G Cybb cytochrome b-245 beta chain JBrowse link X 14,578,330 14,610,049 RGD:6480464
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 JBrowse link 8 62,451,360 62,458,244 RGD:6480464
G Cyp24a1 cytochrome P450, family 24, subfamily a, polypeptide 1 JBrowse link 3 168,097,484 168,111,920 RGD:6480464
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 JBrowse link 1 147,713,879 147,814,410 RGD:6480464
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 JBrowse link 1 213,511,892 213,522,195 RGD:6480464
G Dio1 iodothyronine deiodinase 1 JBrowse link 5 126,894,837 126,911,532 RGD:6480464
G Dio2 iodothyronine deiodinase 2 JBrowse link 6 114,475,156 114,489,443 RGD:6480464
G Dio3 iodothyronine deiodinase 3 JBrowse link 6 134,627,278 134,629,139 RGD:6480464
G Fads1 fatty acid desaturase 1 JBrowse link 1 226,234,034 226,249,118 RGD:6480464
G Fasn fatty acid synthase JBrowse link 10 109,987,735 110,005,901 RGD:6480464
G Gclc glutamate-cysteine ligase, catalytic subunit JBrowse link 8 85,059,051 85,097,471 RGD:6480464
G Gpt glutamic--pyruvic transaminase JBrowse link 7 117,759,083 117,761,932 RGD:6480464
G Gsta1 glutathione S-transferase alpha 1 JBrowse link 9 27,366,404 27,381,004 RGD:6480464
G Hmox1 heme oxygenase 1 JBrowse link 19 14,508,634 14,515,455 RGD:6480464
G Ifng interferon gamma JBrowse link 7 61,337,383 61,341,419 RGD:6480464
G Il1b interleukin 1 beta JBrowse link 3 121,876,256 121,882,637 RGD:6480464
G Il4 interleukin 4 JBrowse link 10 38,963,979 38,969,531 RGD:6480464
G Il6 interleukin 6 JBrowse link 4 3,043,231 3,047,807 RGD:6480464
G Kng2 kininogen 2 JBrowse link 11 81,509,185 81,516,759 RGD:6480464
G Nfe2l2 nuclear factor, erythroid 2-like 2 JBrowse link 3 62,497,568 62,525,146 RGD:6480464
G Nqo1 NAD(P)H quinone dehydrogenase 1 JBrowse link 19 38,422,210 38,437,103 RGD:6480464
G Nr1h2 nuclear receptor subfamily 1, group H, member 2 JBrowse link 1 100,554,577 100,559,896 RGD:6480464
G Nr1h4 nuclear receptor subfamily 1, group H, member 4 JBrowse link 7 30,003,429 30,162,095 RGD:6480464
G Pck1 phosphoenolpyruvate carboxykinase 1 JBrowse link 3 171,213,936 171,219,885 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 Ppard peroxisome proliferator-activated receptor delta JBrowse link 20 7,818,289 7,883,482 RGD:6480464
G Pparg peroxisome proliferator-activated receptor gamma JBrowse link 4 147,274,055 147,399,383 RGD:6480464
G Ptgs2 prostaglandin-endoperoxide synthase 2 JBrowse link 13 67,351,230 67,356,920 RGD:6480464
G Rxra retinoid X receptor alpha JBrowse link 3 6,272,560 6,295,354 RGD:6480464
G Srebf1 sterol regulatory element binding transcription factor 1 JBrowse link 10 46,570,996 46,593,021 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 Ucp2 uncoupling protein 2 JBrowse link 1 165,506,375 165,512,744 RGD:6480464
G Vdr vitamin D receptor JBrowse link 7 139,344,452 139,394,138 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 5 69,857,717 69,983,042 RGD:6480464
G Abcg5 ATP binding cassette subfamily G member 5 JBrowse link 6 7,935,771 7,961,207 RGD:6480464
G Abcg8 ATP binding cassette subfamily G member 8 JBrowse link 6 7,961,413 7,980,708 RGD:6480464
G Cyp27a1 cytochrome P450, family 27, subfamily a, polypeptide 1 JBrowse link 9 81,968,285 81,998,213 RGD:6480464
G Hmgcr 3-hydroxy-3-methylglutaryl-CoA reductase JBrowse link 2 27,480,224 27,500,654 RGD:6480464
G Mttp microsomal triglyceride transfer protein JBrowse link 2 243,366,181 243,407,608 RGD:6480464
G Npc1l1 NPC1 like intracellular cholesterol transporter 1 JBrowse link 14 86,345,946 86,560,694 RGD:6480464
G Scd stearoyl-CoA desaturase JBrowse link 1 264,159,966 264,173,061 RGD:6480464
cholesteryl linolenate term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G Lipc lipase C, hepatic type JBrowse link 8 77,272,582 77,398,485 RGD:6480464
G Lipg lipase G, endothelial type JBrowse link 18 70,903,528 70,924,434 RGD:6480464

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19716
    role 19663
      application 19308
        pharmaceutical 19179
          drug 19179
            nutraceutical 9574
              alpha-linolenic acid 52
                (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 8
                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 19716
    subatomic particle 19712
      composite particle 19712
        hadron 19712
          baryon 19712
            nucleon 19712
              atomic nucleus 19712
                atom 19712
                  main group element atom 19598
                    p-block element atom 19598
                      carbon group element atom 19486
                        carbon atom 19480
                          organic molecular entity 19480
                            organic group 18407
                              organic divalent group 18397
                                organodiyl group 18397
                                  carbonyl group 18285
                                    carbonyl compound 18285
                                      carboxylic acid 17940
                                        monocarboxylic acid 17260
                                          fatty acid 15814
                                            unsaturated fatty acid 894
                                              polyunsaturated fatty acid 652
                                                trienoic fatty acid 102
                                                  fatty acid 18:3 88
                                                    octadecatrienoic acid 88
                                                      linolenic acid 84
                                                        alpha-linolenic acid 52
                                                          (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 8
                                                          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.