(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

CHEBI:15727Reach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol
formateReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
3. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)
Catalysed by PTGS2, KDM1A, KDM1B, ALDH9A1
CHEBI:15746Reach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. diamine N-acetyltransferase (N1-acetylspermine)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 2 routes
1-acylglycerone 3-phosphateReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. Acyl-CoA:glycerone-phosphate O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol
CHEBI:15971Reach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and histidine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes
methanethiolReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
3. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)
Catalysed by PTGS2, KDM1A, KDM1B, SELENBP1
phosphatidylethanolamineReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol
1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol
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
L-cystineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate
2. (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O
3. cystine to cysteine conversion
Catalysed by ALOX12, GPX1, GPX4cytosolOne of 5 routes
11-cis-retinolReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Palmitoyl-CoA:retinol O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 3 routes
cob(II)alaminReach 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 cob(II)alamin + A + 2 H2O + 2 H(+) = 2 aquacob(III)alamin + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, MTRR
phosphatidic acidReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, mitochondrial matrixOne of 7 routes
L-citrullineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of citrulline and cysteine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes
iodideReach 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. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 22 routes
L-valineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and valine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes
L-arginineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of arginine and cysteine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 5 routes
nitric oxideReach 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 nitrite + AH2 + 2 H(+) = 2 nitric oxide + A + 2 H2O
Catalysed by PTGS2, AIFM1, PYROXD1, SUOX
protein polypeptide chainReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. PROTEIN_BS
Catalysed by PTGS2, MOCOScytosol
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
3'-deoxy-3',4'-didehydro-CTPReach 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. CTP + AH2 + S-adenosyl-L-methionine = 3'-deoxy-3',4'-didehydro-CTP + 5'-deoxyadenosine + L-methionine + A + H2O + H(+)
Catalysed by PTGS2, AIFM1, PYROXD1, RSAD2
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
(S)-2-hydroxyglutarateReach 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. (S)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, L2HGDH
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 10 routes
CHEBI:16857Reach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and threonine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes
1-acyl-sn-glycerol 3-phosphateReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrix
a cholesterol esterReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. Acyl-CoA:cholesterol O-acyltransferase
3. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, endoplasmic reticulumOne of 4 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
L-isoleucineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and isoleucine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes
CHEBI:17203Reach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
3. transport of cysteine and proline (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes
anilineReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. Acetyl-CoA:arylamine N-acetyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol
CHEBI:17312Reach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
3. N1,N12-diacetylspermine to N1-acetylspermine conversion
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes
5'-deoxyadenosineReach 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. N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-SH + AH2 + 2 S-adenosyl-L-methionine = 2-methylsulfanyl-N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-H + 5'-deoxyadenosine + L-methionine + A + S-adenosyl-L-homocysteine + 2 H(+)
Catalysed by PTGS2, AIFM1, PYROXD1, CDK5RAP1One of 4 routes
1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
1. long-chain-fatty-acid-CoA ligase (EPA)
2. acyl-CoA pool formation and breakdown
3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol
1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach 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. Lecithin Retinol Acyltransferase
Catalysed by PTGS2, RETSAT, LRATcytosol
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
all-trans-retinyl hexadecanoateReach 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 + hexadecanoyl-CoA = all-trans-retinyl hexadecanoate + CoA
Catalysed by PTGS2, RETSAT, DGAT1, PNPLA4 and 3 moreOne of 2 routes
3,3',5'-triiodo-L-thyronine sulfateReach 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. 3,3',5'-triiodo-L-thyronine sulfate + iodide + A + H(+) = L-thyroxine sulfate + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1
3,3'-diiodo-L-thyronineReach 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. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes
3,3'-diiodo-L-thyronine sulfateReach 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. 3,3'-diiodo-L-thyronine sulfate + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine sulfate + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1One of 2 routes
(7Z,10Z,13Z)-hexadecatrienoyl-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 (C18:3->C16:3), Mitochondrial
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrix
CHEBI:17724Reach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
3. dimethylglycine dehydrogenase (formaldehyde)
Catalysed by PTGS2, KDM1A, KDM1B, PDPR and 1 morecytosol
glycine betaineReach from here →
1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. choline + A = betaine aldehyde + AH2
3. p-cumic alcohol:NAD+ oxidoreductase
Catalysed by PTGS2, CHDH, ALDH7A1cytosolOne of 4 routes
a 1,2-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 1,2-diacyl-sn-glycerol + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 3 routes