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C20H32O2 Arachidonic acid 304.24023 CHEBI:15843 ChEBI 1.0 CHEBI:77527 ChEBI CHEBI:77526 ChEBI CHEBI:28125 ChEBI P0C869 UniProt Gamma-Linolenic acid SMILES CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C CHEBI:28364 ChEBI 24880-45-3 CAS Linoleic acid C06428 KEGG Compound CHEBI:17351 ChEBI C06429 KEGG Compound C06426 KEGG Compound CPD-7421 BioCyc C06427 KEGG Compound HMDB06246 HMDB Elongation of very long chain fatty acids protein 5 D-HEXOSE-6-PHOSPHATE BioCyc 1.0 1.0 1.0 1.0 Fatty acid desaturase 2 Arachidonic acid C00219 KEGG Compound 506-26-3 CAS C20H30O2 Eicosapentaenoic acid 302.22458 Elongation of very long chain fatty acids protein 4 PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) C22H34O2 Docosapentaenoic acid 330.2559 C24H36O2 Tetracosahexaenoic acid 356.27155 C20H32O2 Cis-8,11,14,17-Eicosatetraenoic acid 304.24023 Tetracosatetraenoic acid (24:4n-6) 1.0 Linoleic acid HMDB03073 HMDB 52922845 PubChem-compound 10417-94-4 CAS C22H32O2 Docosahexaenoic acid 328.24023 SMP00051 SMPDB C24H40O2 Tetracosatetraenoic acid (24:4n-6) 360.30283 SMILES CCCCCC=CCC=CCC=CCCCCC(O)=O SubPathwayInteraction4 SubPathway4Reaction SubPathwayReaction SubPathwayInteraction3 SubPathwayReaction SubPathway3Reaction 5280934 PubChem-compound 5280933 PubChem-compound 28874-58-0 CAS 4444199 ChemSpider CPD-4223 BioCyc 1.0 5Z13E-15S-91115-TRIHYDROXYPROSTA- BioCyc SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O C18H28O2 Stearidonic acid 276.20892 PHOSPHATIDYLCHOLINE BioCyc SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O Linoleic acid SMILES CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O 25448-00-4 CAS 1.14.19.- false 1.14.19.- 8,11,14-Eicosatrienoic acid → Arachidonic acid LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Arachidonic acid → Adrenic acid LEFT_TO_RIGHT 1.14.19.- false 1.14.19.- Tetracosapentaenoic acid (24:5n-3) → Tetracosahexaenoic acid LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Gamma-Linolenic acid → 8,11,14-Eicosatrienoic acid LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Eicosapentaenoic acid → Docosapentaenoic acid LEFT_TO_RIGHT 1.0 2.3.1.199 false 2.3.1.199 Docosapentaenoic acid → Tetracosapentaenoic acid (24:5n-3) LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Stearidonic acid → Cis-8,11,14,17-Eicosatetraenoic acid LEFT_TO_RIGHT 1.14.19.- false 1.14.19.- Cis-8,11,14,17-Eicosatetraenoic acid → Eicosapentaenoic acid LEFT_TO_RIGHT HMDB06323 HMDB 2.3.1.199 false 2.3.1.199 Adrenic acid → Tetracosatetraenoic acid (24:4n-6) LEFT_TO_RIGHT HMDB06322 HMDB SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O GO:0005759 GENE ONTOLOGY 14505435 PubChem-compound 1.14.19.- false 1.14.19.- Linoleic acid → Gamma-Linolenic acid LEFT_TO_RIGHT Alpha-Linolenic acid HMDB00673 HMDB 9897310 ChemSpider Docosapentaenoic acid 5280581 PubChem-compound CPD-7196 BioCyc 444899 PubChem-compound Extracellular Space Stearidonic acid 1.0 HMDB02177 HMDB Eicosapentaenoic acid 4593750 ChemSpider SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O 1.14.19.- false 1.14.19.- Tetracosatetraenoic acid (24:4n-6) → Tetracosapentaenoic acid (24:5n-6) LEFT_TO_RIGHT 4945614 ChemSpider 3.1.1.4 false 3.1.1.4 PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) → Alpha-Linolenic acid + Linoleic acid LEFT_TO_RIGHT 1.0 393682 ChemSpider 446284 PubChem-compound HMDB06547 HMDB 5497182 PubChem-compound 5497181 PubChem-compound SMP00018 SMPDB ReactionCatalysis85 ACTIVATION HMDB02183 HMDB C01595 KEGG Compound 5280450 PubChem-compound ReactionCatalysis86 ACTIVATION ReactionCatalysis83 ACTIVATION ReactionCatalysis84 ACTIVATION ReactionCatalysis89 ACTIVATION ReactionCatalysis87 ACTIVATION ReactionCatalysis88 ACTIVATION Fatty acid desaturase 2 GO:0005615 GENE ONTOLOGY GO:0005737 GENE ONTOLOGY Alpha-Linolenic acid 4593749 ChemSpider Cytosolic phospholipase A2 beta Q9NYP7 UniProt Endoplasmic Reticulum CL:0000000 CELL TYPE ONTOLOGY ReactionCatalysis94 ACTIVATION ReactionCatalysis95 ACTIVATION 4471933 ChemSpider C00157 KEGG Compound Transport2 false Alpha-Linolenic acid (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT CHEBI:27432 ChEBI Transport3 false Linoleic acid (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT Docosahexaenoic acid SubPathwayOutput ReactionCatalysis92 ACTIVATION ReactionCatalysis93 ACTIVATION ReactionCatalysis90 ACTIVATION ReactionCatalysis91 ACTIVATION 1.14.19.- false 1.14.19.- Alpha-Linolenic acid → Stearidonic acid LEFT_TO_RIGHT Fatty acid desaturase 1 Mitochondrial Matrix 4444436 ChemSpider 392692 ChemSpider 4444437 ChemSpider HMDB01999 HMDB HMDB06528 HMDB 1.0 1.0 Elongation of very long chain fatty acids protein 5 CHEBI:77366 ChEBI LINOLENIC_ACID BioCyc C18H30O2 Gamma-Linolenic acid 278.22458 Cytoplasm CHEBI:77360 ChEBI Docosapentaenoic acid (22n-6) SubPathwayOutput 1.0 Cell SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O Cytosolic phospholipase A2 beta HMDB01043 HMDB C20H34O2 8,11,14-Eicosatrienoic acid 306.2559 C16513 KEGG Compound HMDB02925 HMDB C18H32O2 Linoleic acid 280.24023 GO:0005783 GENE ONTOLOGY C24H38O2 Tetracosapentaenoic acid (24:5n-6) 358.28717 C24H38O2 Tetracosapentaenoic acid (24:5n-3) 358.28717 8,11,14-Eicosatrienoic acid 1783-84-2 CAS HMDB01976 HMDB Adrenic acid O95864 UniProt C22H36O2 Adrenic acid 332.27155 BiologicalState18 1.0 Fatty acid desaturase 1 Tetracosapentaenoic acid (24:5n-6) SubPathwayInput O60427 UniProt 60-33-3 CAS Cis-8,11,14,17-Eicosatetraenoic acid C16527 KEGG Compound C18H30O2 Alpha-Linolenic acid 278.22458 HMDB01388 HMDB 9606 TAXONOMY PW000023 PathWhiz 11792612 PubChem-compound 1.0 52921800 PubChem-compound CHEBI:32389 ChEBI 52921801 PubChem-compound CHEBI:53486 ChEBI SMILES CCCCCC=CCC=CCC=CCCCCCCC(O)=O CHEBI:53487 ChEBI 393183 ChemSpider 6441454 PubChem-compound SMILES CCCCC\C=C/C\C=C/CCCCCCCC(O)=O C22H34O2 Docosapentaenoic acid (22n-6) 330.2559 6217-54-5 CAS 9967286 ChemSpider BiologicalState8 Alpha Linolenic Acid and Linoleic Acid Metabolism 81247-23-6 CAS Tetracosahexaenoic acid SubPathwayInput 4444105 ChemSpider SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O 30776541 ChemSpider HMDB02007 HMDB 20290-75-9 CAS 1.0 1.0 5312508 PubChem-compound SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O CHEBI:53488 ChEBI C03242 KEGG Compound C16300 KEGG Compound SMILES CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O 445580 PubChem-compound PW000006 PathWhiz CPD-6941 BioCyc Alpha-Linolenic acid CHEBI:71488 ChEBI SMILES CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O 30776538 ChemSpider Elongation of very long chain fatty acids protein 4 1.0 Fatty acid Metabolism SubPathway 30776540 ChemSpider CHEBI:28661 ChEBI 24880-40-8 CAS C44H78NO8P PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) 779.5465 Fatty acid Metabolism SubPathway CHEBI:65136 ChEBI 1.0 506-32-1 CAS HMDB02226 HMDB 463-40-1 CAS 24766866 ChemSpider 11722594 PubChem-compound HMDB08204 HMDB Q9GZR5 UniProt ARACHIDONIC_ACID BioCyc Tetracosapentaenoic acid (24:5n-3) Fatty acid desaturase 2 Elongation of very long chain fatty acids protein 5 Fatty acid desaturase 1 Elongation of very long chain fatty acids protein 5 Elongation of very long chain fatty acids protein 4 Fatty acid desaturase 2 Cytosolic phospholipase A2 beta Tetracosahexaenoic acid Docosahexaenoic acid Tetracosapentaenoic acid (24:5n-6) Docosapentaenoic acid (22n-6) Alpha-Linolenic acid Alpha-Linolenic acid Linoleic acid Linoleic acid Stearidonic acid Cis-8,11,14,17- Eicosatetraenoic acid Eicosapentaenoic acid Docosapentaenoic acid Gamma-Linolenic acid Tetracosapentaenoic acid (24:5n-3) 8,11,14-Eicosatrienoic acid Arachidonic acid Adrenic acid Tetracosatetraenoic acid (24:4n-6) PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) Calcium Fatty acid Metabolism Fatty acid Metabolism Extracellular Space Intracellular Space Endoplasmic Reticulum Mitochondria Mitochondria Endoplasmic Reticulum
C20H32O2 Arachidonic acid 304.24023 CHEBI:15843 ChEBI 1.0 CHEBI:77527 ChEBI CHEBI:77526 ChEBI CHEBI:28125 ChEBI P0C869 UniProt Gamma-Linolenic acid SMILES CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C CHEBI:28364 ChEBI 24880-45-3 CAS Linoleic acid C06428 KEGG Compound CHEBI:17351 ChEBI C06429 KEGG Compound C06426 KEGG Compound CPD-7421 BioCyc C06427 KEGG Compound HMDB06246 HMDB Elongation of very long chain fatty acids protein 5 D-HEXOSE-6-PHOSPHATE BioCyc 1.0 1.0 1.0 1.0 Fatty acid desaturase 2 Arachidonic acid C00219 KEGG Compound 506-26-3 CAS C20H30O2 Eicosapentaenoic acid 302.22458 Elongation of very long chain fatty acids protein 4 PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) C22H34O2 Docosapentaenoic acid 330.2559 C24H36O2 Tetracosahexaenoic acid 356.27155 C20H32O2 Cis-8,11,14,17-Eicosatetraenoic acid 304.24023 Tetracosatetraenoic acid (24:4n-6) 1.0 Linoleic acid HMDB03073 HMDB 52922845 PubChem-compound 10417-94-4 CAS C22H32O2 Docosahexaenoic acid 328.24023 http://identifiers.org/smpdb/SMP00051 SMPDB C24H40O2 Tetracosatetraenoic acid (24:4n-6) 360.30283 SMILES CCCCCC=CCC=CCC=CCCCCC(O)=O SubPathwayInteraction4 SubPathway4Reaction SubPathwayReaction SubPathwayInteraction3 SubPathwayReaction SubPathway3Reaction 5280934 PubChem-compound 5280933 PubChem-compound 28874-58-0 CAS 4444199 ChemSpider CPD-4223 BioCyc 1.0 5Z13E-15S-91115-TRIHYDROXYPROSTA- BioCyc SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O C18H28O2 Stearidonic acid 276.20892 PHOSPHATIDYLCHOLINE BioCyc SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O Linoleic acid SMILES CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O 25448-00-4 CAS 1.14.19.- false 1.14.19.- 8,11,14-Eicosatrienoic acid → Arachidonic acid LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Arachidonic acid → Adrenic acid LEFT_TO_RIGHT 1.14.19.- false 1.14.19.- Tetracosapentaenoic acid (24:5n-3) → Tetracosahexaenoic acid LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Gamma-Linolenic acid → 8,11,14-Eicosatrienoic acid LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Eicosapentaenoic acid → Docosapentaenoic acid LEFT_TO_RIGHT 1.0 2.3.1.199 false 2.3.1.199 Docosapentaenoic acid → Tetracosapentaenoic acid (24:5n-3) LEFT_TO_RIGHT 2.3.1.199 false 2.3.1.199 Stearidonic acid → Cis-8,11,14,17-Eicosatetraenoic acid LEFT_TO_RIGHT 1.14.19.- false 1.14.19.- Cis-8,11,14,17-Eicosatetraenoic acid → Eicosapentaenoic acid LEFT_TO_RIGHT HMDB06323 HMDB 2.3.1.199 false 2.3.1.199 Adrenic acid → Tetracosatetraenoic acid (24:4n-6) LEFT_TO_RIGHT HMDB06322 HMDB SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O GO:0005759 GENE ONTOLOGY 14505435 PubChem-compound 1.14.19.- false 1.14.19.- Linoleic acid → Gamma-Linolenic acid LEFT_TO_RIGHT Alpha-Linolenic acid HMDB00673 HMDB 9897310 ChemSpider Docosapentaenoic acid 5280581 PubChem-compound CPD-7196 BioCyc 444899 PubChem-compound Extracellular Space Stearidonic acid 1.0 HMDB02177 HMDB Eicosapentaenoic acid 4593750 ChemSpider SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O 1.14.19.- false 1.14.19.- Tetracosatetraenoic acid (24:4n-6) → Tetracosapentaenoic acid (24:5n-6) LEFT_TO_RIGHT 4945614 ChemSpider 3.1.1.4 false 3.1.1.4 PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) → Alpha-Linolenic acid + Linoleic acid LEFT_TO_RIGHT 1.0 393682 ChemSpider 446284 PubChem-compound HMDB06547 HMDB 5497182 PubChem-compound 5497181 PubChem-compound http://identifiers.org/smpdb/SMP00018 SMPDB ReactionCatalysis85 ACTIVATION HMDB02183 HMDB C01595 KEGG Compound 5280450 PubChem-compound ReactionCatalysis86 ACTIVATION ReactionCatalysis83 ACTIVATION ReactionCatalysis84 ACTIVATION ReactionCatalysis89 ACTIVATION ReactionCatalysis87 ACTIVATION ReactionCatalysis88 ACTIVATION Fatty acid desaturase 2 GO:0005615 GENE ONTOLOGY GO:0005737 GENE ONTOLOGY Alpha-Linolenic acid 4593749 ChemSpider Cytosolic phospholipase A2 beta Q9NYP7 UniProt Endoplasmic Reticulum CL:0000000 CELL TYPE ONTOLOGY ReactionCatalysis94 ACTIVATION ReactionCatalysis95 ACTIVATION 4471933 ChemSpider C00157 KEGG Compound Transport2 false Alpha-Linolenic acid (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT CHEBI:27432 ChEBI Transport3 false Linoleic acid (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT Docosahexaenoic acid SubPathwayOutput ReactionCatalysis92 ACTIVATION ReactionCatalysis93 ACTIVATION ReactionCatalysis90 ACTIVATION ReactionCatalysis91 ACTIVATION 1.14.19.- false 1.14.19.- Alpha-Linolenic acid → Stearidonic acid LEFT_TO_RIGHT Fatty acid desaturase 1 Mitochondrial Matrix 4444436 ChemSpider 392692 ChemSpider 4444437 ChemSpider HMDB01999 HMDB HMDB06528 HMDB 1.0 1.0 Elongation of very long chain fatty acids protein 5 CHEBI:77366 ChEBI LINOLENIC_ACID BioCyc C18H30O2 Gamma-Linolenic acid 278.22458 Cytoplasm CHEBI:77360 ChEBI Docosapentaenoic acid (22n-6) SubPathwayOutput 1.0 Cell SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O Cytosolic phospholipase A2 beta HMDB01043 HMDB C20H34O2 8,11,14-Eicosatrienoic acid 306.2559 C16513 KEGG Compound HMDB02925 HMDB C18H32O2 Linoleic acid 280.24023 GO:0005783 GENE ONTOLOGY C24H38O2 Tetracosapentaenoic acid (24:5n-6) 358.28717 C24H38O2 Tetracosapentaenoic acid (24:5n-3) 358.28717 8,11,14-Eicosatrienoic acid 1783-84-2 CAS HMDB01976 HMDB Adrenic acid O95864 UniProt C22H36O2 Adrenic acid 332.27155 BiologicalState18 Homo sapiens, Cell, Endoplasmic Reticulum 1.0 Fatty acid desaturase 1 Tetracosapentaenoic acid (24:5n-6) SubPathwayInput O60427 UniProt 60-33-3 CAS Cis-8,11,14,17-Eicosatetraenoic acid C16527 KEGG Compound C18H30O2 Alpha-Linolenic acid 278.22458 HMDB01388 HMDB 9606 TAXONOMY PW000023 PathWhiz 11792612 PubChem-compound 1.0 52921800 PubChem-compound CHEBI:32389 ChEBI 52921801 PubChem-compound CHEBI:53486 ChEBI SMILES CCCCCC=CCC=CCC=CCCCCCCC(O)=O CHEBI:53487 ChEBI 393183 ChemSpider 6441454 PubChem-compound SMILES CCCCC\C=C/C\C=C/CCCCCCCC(O)=O C22H34O2 Docosapentaenoic acid (22n-6) 330.2559 6217-54-5 CAS 9967286 ChemSpider BiologicalState8 Homo sapiens, Cell, Cytoplasm Alpha Linolenic Acid and Linoleic Acid Metabolism 81247-23-6 CAS Tetracosahexaenoic acid SubPathwayInput 4444105 ChemSpider SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O 30776541 ChemSpider HMDB02007 HMDB 20290-75-9 CAS 1.0 1.0 5312508 PubChem-compound SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O CHEBI:53488 ChEBI C03242 KEGG Compound C16300 KEGG Compound SMILES CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O 445580 PubChem-compound PW000006 PathWhiz CPD-6941 BioCyc Alpha-Linolenic acid CHEBI:71488 ChEBI SMILES CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O 30776538 ChemSpider Elongation of very long chain fatty acids protein 4 1.0 Fatty acid Metabolism SubPathway 30776540 ChemSpider CHEBI:28661 ChEBI 24880-40-8 CAS C44H78NO8P PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) 779.5465 Fatty acid Metabolism SubPathway CHEBI:65136 ChEBI 1.0 506-32-1 CAS HMDB02226 HMDB 463-40-1 CAS 24766866 ChemSpider 11722594 PubChem-compound HMDB08204 HMDB Q9GZR5 UniProt ARACHIDONIC_ACID BioCyc Tetracosapentaenoic acid (24:5n-3) Endoplasmic Reticulum Mitochondria FADS2 ELOVL5 FADS1 ELOVL5 ELOVL4 FADS2 PLA2G4B Tetracosahexaenoic acid Docosahexaenoic acid Tetracosapentaenoic acid (24:5n-6) Docosapentaenoic acid (22n-6) Alpha-Linolenic acid Alpha-Linolenic acid Linoleic acid Linoleic acid Stearidonic acid Cis- 8,11,14,17- Eicosatetraenoic acid Eicosapentaenoic acid Docosapentaenoic acid Gamma-Linolenic acid Tetracosapentaenoic acid (24:5n-3) 8,11,14- Eicosatrienoic acid Arachidonic acid Adrenic acid Tetracosatetraenoic acid (24:4n-6) PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) Fatty acid Metabolism Fatty acid Metabolism