alpha-linolenic acid
362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API
374 compounds within 3 steps: 4 in 1, 45 in 2, 325 in 3
Three steps
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 4 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (14R,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 4 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (11S,12R)-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C8, CYP2C9, CYP2C19, CYP2J2 and 1 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (11R,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP2C8, CYP2D6, CYP2C9 and 3 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP2D6, CYP2C9, CYP2C19 and 2 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 4 routes
- Utilized Transport
- transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
- butanoyl-CoA + H2O = S-butanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)
Catalysed by SLC33A1, ESCO2, OXSM, NUDT19 and 2 moreendoplasmic reticulum, cytosol, mitochondrial matrix
- Long-Chain-Fatty-Acid-Coa Ligase
- Beta Oxidation of Fatty Acid
- octanoyl-CoA + H2O = S-octanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 moreendoplasmic reticulum, mitochondrial matrix
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- DHA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 21-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate[r]
Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- myristic acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 13-hydroxytetradecanoate[r]
Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1
Catalysed by PTGS2cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + 2 O2 = prostaglandin G3
Catalysed by PTGS2cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + O2 = 14-hydroperoxy-(7Z,10Z,12E,16Z,19Z)-docosapentaenoate
Catalysed by ALOX15cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate
Catalysed by ALOX15cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate
Catalysed by ALOX15cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- transport of arachidonate (cytosol to extracellular)
Catalysed by SLCO1B1cytosol, extracellular spaceOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
Catalysed by PM20D1cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 3 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP3A4, CYP2C8, CYP2D6 and 2 morecytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular space
- Long-Chain-Fatty-Acid-Coa Ligase
- Beta Oxidation of Fatty Acid
- octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moreendoplasmic reticulum, mitochondrial matrix
- Long-Chain-Fatty-Acid-Coa Ligase
- Beta Oxidation of Fatty Acid
- octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moreendoplasmic reticulum, mitochondrial matrix
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
No catalyst recordedcytosol, extracellular spaceOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + H2O = 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H(+)
Catalysed by DAGLBcytosol, extracellular space
- long-chain-fatty-acid-CoA ligase (linolenate)
- Linolenoyl-CoA hydrolase
- carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes