all-cis-docosa-4,7,10,13,16,19-hexaenoic acid

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

465 compounds within 3 steps: 20 in 1, 54 in 2, 391 in 3

Three steps

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
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
(13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (13R)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1, PTGS1
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
(13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate
2. (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate = (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + H2O
3. (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + glutathione = (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate
Catalysed by ALOX5, ALOX15, ALOX12, GSTM4 and 1 more
2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. 2-(prostaglandin G2)-sn-glycero-3-phosphoethanolamine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamine + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. A + NADH + H(+) = AH2 + NAD(+)
3. 2-(prostaglandin G2)-sn-glycero-3-phosphocholine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphocholine + A + H2O
Catalysed by PTGS2, AIFM1, PYROXD1
11-cis-retinyl tetradecanoateReach from here →
1. 11-peroxy-docosahexaenoate to DHA conversion
2. Palmitoyl-CoA:retinol O-acyltransferase
3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA
Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosol
all-trans-retinyl tetradecanoateReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA
Catalysed by PTGS2, RETSAT, AWAT2
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
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
(7Z)-octadecenoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes
CHEBI:15345Reach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Acetoacetate:CoA ligase (AMP-forming)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes
cholineReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Acetyl-CoA:choline O-acetyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, nucleus
pyruvateReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. L-cysteine hydrogen-sulfide-lyase (deaminating
Catalysed by PTGS2, MOCOS, CTHcytosolOne of 6 routes
CHEBI:15380Reach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 8 routes
CHEBI:15477Reach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. glycine N-acyltransferase (2-methylbutyryl-CoA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 2 routes
2-methylcrotonoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Production of Tiglylcarnitine
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes
isobutyryl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 3 routes
3-methylbut-2-enoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. glycine-N-acyltransferase (3-methylcrotonoylglycine)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix
isovaleryl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. glycine N-acyltransferase (isovalerylglycine)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 3 routes
arachidonoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Arachidonate:CoA ligase (AMP-forming)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 17 routes
CHEBI:15519Reach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. propanoyl-CoA C-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, peroxisomeOne of 2 routes
oleoyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Transport of octadecenoyl-CoA into Mitochondrial Matrix
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 15 routes
phenylacetyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Phenylacetate:CoA ligase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 3 routes
propionyl-CoAReach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. Propanoate:CoA ligase (AMP-forming)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 43 routes
(S)-malateReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. (R)-malate + A = oxaloacetate + AH2
3. transport of malate and OAA (cytosol to mitochondria)
Catalysed by PTGS2, D2HGDHmitochondrial matrix, cytosolOne of 5 routes
L-leucineReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and leucine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A9, SLC3A1extracellular space, cytosolOne of 3 routes
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 5 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
CHEBI:15650Reach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. N-acetyl-LTE4 to leukotriene E4 conversion
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 38 morecytosolOne of 2 routes
all-trans-3-hydroxyretinolReach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
3. all-trans-retinol + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-3-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O
Catalysed by PTGS2, RETSAT, CYP27C1
CHEBI:15699Reach from here →
1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and homoserine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes
CHEBI:15727Reach from here →
1. long-chain-fatty-acid-CoA ligase (DHA)
2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol