(5Z,8Z,11Z)-eicosatrienoate

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

200 compounds within 3 steps: 1 in 1, 25 in 2, 174 in 3

Three steps

16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoateReach 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 = 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoateReach 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 = 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoateReach 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 = 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
19,20-epoxy-(7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19,20-epoxy-(7Z,10Z,13Z,16Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
16,17-epoxy-(7Z,10Z,13Z,19Z)-docosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16,17-epoxy-(7Z,10Z,13Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
13,14-epoxy-(7Z,10Z,16Z,19Z)-docosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13,14-epoxy-(7Z,10Z,16Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
10,11-epoxy-(7Z,13Z,16Z,19Z)-docosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10,11-epoxy-(7Z,13Z,16Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4F8, CYP4F12cytosol, extracellular space
2,4-dinitrophenyl-S-glutathioneReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. transport of arachidonate (cytosol to extracellular)
Catalysed by SLCO1B1cytosol, extracellular spaceOne of 2 routes
N-(9Z-octadecenoyl)-L-phenylalanineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular space
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular space
N-(9Z-octadecenoyl)-L-leucineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
Catalysed by PM20D1cytosol, extracellular space
(19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach 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 = (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
(19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach 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 = (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
8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (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
11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C8, CYP2C9cytosol, extracellular space
14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C8, CYP2C9cytosol, extracellular space
7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach 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 2 routes
13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach 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 2 routes
13(S)-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 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach 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 space
8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
No catalyst recordedcytosol, extracellular spaceOne of 2 routes
1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 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
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine
Catalysed by FAAH, PM20D1cytosol, extracellular space
arachidonoyl-CoAReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Arachidonate:CoA ligase (AMP-forming)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, extracellular spaceOne of 3 routes
palmitoyl-CoAReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Palmitate:CoA ligase (AMP-forming)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, extracellular spaceOne of 3 routes
oleoyl-CoAReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. long-chain-fatty-acid-CoA ligase (oleate)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, extracellular spaceOne of 3 routes
(7S)-hydroperoxy-(4Z,8E,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 + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate
Catalysed by ALOX5cytosol, extracellular space
(11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate
Catalysed by ALOX15cytosol, extracellular space
12(S)-HPETEReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. arachidonate:oxygen 12-oxidoreductase
Catalysed by ALOX12cytosol, extracellular spaceOne of 4 routes
15(S)-HPETEReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. arachidonate:oxygen 15-oxidoreductase
Catalysed by ALOX15B, ALOX15cytosol, extracellular spaceOne of 4 routes
5(S)-HPETEReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. Arachidonate:oxygen 5-oxidoreductase
Catalysed by ALOX5cytosol, extracellular space
11-cis-retinyl hexadecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 11-peroxy-docosahexaenoate to DHA conversion
No catalyst recordedcytosol, extracellular spaceOne of 3 routes
CHEBI:16566Reach from here →
1. (10Z)-heptadecenoic acid formation
2. N-acylsphingosine amidohydrolase
3. N-acylsphingosine amidohydrolase
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol
8-hydroxydodecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
10-hydroxydodecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
9-hydroxydodecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
9-hydroxytetradecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
10-hydroxytetradecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
12-hydroxytetradecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 12-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
11-hydroxytetradecanoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP4Z1cytosol, extracellular space
CHEBI:16856Reach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. transport of arachidonate and GSH (cytosol to extracellular)
No catalyst recordedcytosol, extracellular spaceOne of 2 routes
octadecanalReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)
Catalysed by ALDH3A2cytosol, extracellular space
hexadecanalReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]
Catalysed by ALDH3B1, ALDH3B2, ALDH3A2cytosol, extracellular spaceOne of 2 routes
a 1,2-diacyl-sn-glycerolReach 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 morecytosolOne of 2 routes
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate
Catalysed by ALOX5cytosol, extracellular space
O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP
Catalysed by UGT1A9, UGT2B7, UGT1A6, UGT1A1 and 2 morecytosol, extracellular space
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. fatty acylamide amidohydrolase
Catalysed by FAAHcytosol, extracellular space
dodecanalReach from here →
1. (10Z)-heptadecenoic acid formation
2. (10Z)-heptadecenoic acid formation
3. 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]
Catalysed by ALDH3A2cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
a fatty acidReach from here →
1. (10Z)-heptadecenoic acid formation
2. N-acylsphingosine amidohydrolase
3. an N-acylsphinganine + H2O = sphinganine + a fatty acid
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol
an N-acyl-(4R)-4-hydroxysphinganineReach from here →
1. (10Z)-heptadecenoic acid formation
2. N-acylsphingosine amidohydrolase
3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 2 routes