(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate

362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API

443 compounds within 3 steps: 19 in 1, 50 in 2, 374 in 3

Three steps

(13Z)-docosenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes
(11Z)-eicosenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 10 routes
(9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 5 routes
(15Z)-tetracosenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (nervonic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 9 routes
(17Z)-hexacosenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (ximenic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes
(8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes
(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (DHA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 13 routes
heptadecanoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (margaric acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes
(9Z)-heptadecenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes
(11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes
N-(15Z-tetracosenoyl)-sphing-4-enineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
Catalysed by ACER2, ACER1, ASAH2cytosol, extracellular space
nonadecanoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes
(11Z)-octadecenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 3 routes
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
Catalysed by ALOX12Bcytosol, extracellular space
(8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Arachidonate:oxygen 8-oxidoreductase
Catalysed by ALOX12cytosol, extracellular spaceOne of 2 routes
1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
Catalysed by ABHD11cytosol, extracellular space
a 2,3-diacyl-sn-glycerolReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. a 2-acylglycerol + an acyl-CoA = a 2,3-diacyl-sn-glycerol + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol
2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. fatty acid amide hydrolase (arachidonate)
Catalysed by FAAHcytosol, extracellular space
(R)-2-hydroxytetracosanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetracosanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxytetracosanoate + 2 Fe(III)-[cytochrome b5] + H2O
Catalysed by FA2Hcytosol, extracellular space
di-(9Z)-octadecenoylglycerolReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol
Catalysed by PTGS2, RETSAT, PNPLA4, PNPLA2
2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
3. all-trans-retinol + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = all-trans-retinyl hexadecanoate + 2-hexadecanoyl-sn-glycero-3-phosphocholine
Catalysed by PTGS2, RETSAT, LRAT
1-O-alkyl-3-acylglycerolReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. 1-O-alkylglycerol + an acyl-CoA = 1-O-alkyl-3-acylglycerol + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol
docosanedioateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Fatty Acid Omega Oxidation by Hydroxylases (C22->C22Dc), Endoplasmatic Reticulum
Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulum
dodecanedioyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Activation of dodecanedioic acid
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes
decanedioyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Production of Sebacoylcarnitine
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes
octanedioyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Production of Suberylcarnitine
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes
hexanedioyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Activation of adipic acid for Formation of Adipoyl Carnitine
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes
(4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes
(11Z,14Z)-eicosadienoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes
(R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Production of 3-Hydroxyoctadecenoylcarnitinec
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol
(13Z)-eicosenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes
24-hydroxytetracosanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetracosanoate + reduced [NADPH--hemoprotein reductase] + O2 = 24-hydroxytetracosanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F2, CYP4F3cytosol, extracellular space
20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. arachidonic acid:oxygen 1-oxidoreductase
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 23 morecytosol, extracellular spaceOne of 3 routes
11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP1A2, CYP2C9, CYP2C19 and 1 morecytosol, extracellular space
11-hydroxydodecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. lauric acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 11-hydroxydodecanoate[r]
Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
22-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 22-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F2, CYP4F3, CYP4V2, CYP4F11cytosol, extracellular space
14-hydroxytetradecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. alkane 1-monooxygenase (myristic acid)
Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes
4,8-dimethylnonanoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, peroxisomeOne of 3 routes
tetradecanedioyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, peroxisome
hexadecanedioyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Production of Hexadecanedioylcarnitine
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)
Catalysed by ABHD11cytosol, extracellular space
pristanoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. fatty-acid-CoA ligase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes
a 1,3-diacyl-sn-glycerolReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. a 3-acyl-sn-glycerol + an acyl-CoA = a 1,3-diacyl-sn-glycerol + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes
a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholineReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol
a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol
undecanoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. medium-chain acyl-CoA ligase (undecylic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosolOne of 3 routes
(9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9S)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1, PTGS1