(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

(9R)-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 = (9R)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1, PTGS1
N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol, extracellular space
N-dodecanoyl-(4R)-hydroxysphinganineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. N-dodecanoyl-(4R)-hydroxysphinganine + H2O = (4R)-hydroxysphinganine + dodecanoate
Catalysed by ASAH1cytosol, extracellular space
(14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate
Catalysed by ALOX5, ALOX15, ALOX12cytosol, extracellular space
9-cis-retinolReach 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. retinol binding protein (retinol)
Catalysed by PTGS2, RETSAT, RBP1, RBP2cytosolOne of 2 routes
18-hydroxy-(9Z)-octadecenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (9Z)-octadecenoate + reduced [NADPH--hemoprotein reductase] + O2 = 18-hydroxy-(9Z)-octadecenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4A11, CYP4F11cytosol, extracellular space
an N-acylsphinganine-1-phosphoethanolamineReach from here →
1. (10Z)-heptadecenoic acid formation
2. N-acylsphingosine amidohydrolase
3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol
1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
Catalysed by ABHD12cytosol, extracellular space
(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular spaceOne of 3 routes
(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular spaceOne of 3 routes
(15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by PTGS2cytosol, extracellular space
11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Arachidonate: oxygen 11-oxidoreductase
Catalysed by ALOX12cytosol, extracellular spaceOne of 2 routes
prostaglandin G2Reach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Arachidonate:oxygen oxidoreductase
Catalysed by PTGS1, PTGS2cytosol, extracellular space, endoplasmic reticulumOne of 2 routes
thio-Mo-molybdopterinReach 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. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1, MOCOSOne of 3 routes
14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate
Catalysed by ALOX12Bcytosol, extracellular space
(12R)-hydroxy-(5Z,8Z,10E,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 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 23 morecytosol, extracellular spaceOne of 4 routes
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. unspecific monooxygenase (arachidonate)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 3 routes
tetradecanalReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetradecanal + NAD(+) + H2O = tetradecanoate + NADH + 2 H(+)
Catalysed by ALDH3A2cytosol, extracellular space
1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
Catalysed by ABHD16Acytosol, extracellular space
1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
Catalysed by ABHD16Acytosol, extracellular space
1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
Catalysed by ABHD16Acytosol, extracellular space
(5Z)-tetradecenoyl-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 (physeteric acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 9 routes
(3E)-decenoyl-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 (C12:1->C10:1), Mitochondrial
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrix
7-hydroxydodecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 7-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
2-glyceryl-prostaglandin H2Reach 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. 2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
N-(dodecanoyl)-sphinganineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. N-(dodecanoyl)-sphinganine + H2O = dodecanoate + sphinganine
Catalysed by ASAH1cytosol, extracellular space
(2R,6)-dimethylheptanoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrix
an N(2)-acyl-L-glutamineReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol
(7Z)-hexadecenoyl-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 (7-palmitoleic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 9 routes
tricosanoyl-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 (tricosanoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes
a 3-oxoacyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol
(18R)-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 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8cytosol, extracellular space
prostaglandin H1Reach 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. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
(5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach 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. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
(5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach 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. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
(5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach 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. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular spaceOne of 2 routes
13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular spaceOne of 2 routes
15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by ALOX15Bcytosol, extracellular space
5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
Catalysed by ALOX15Bcytosol, extracellular space
13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular spaceOne of 2 routes
(13S)-hydroxy-(9Z,11E)-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 = (13S)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1, PTGS1