(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
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
- transport of cysteine and tyrosine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
- retinol: NADP+ oxidoreductase
Catalysed by PTGS2, RETSAT, DHRS3, RDH10 and 4 morecytosolOne of 6 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
- transport of cysteine and lysine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
- transport of cysteine and glutamine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC3A2, SLC7A5 and 1 moreextracellular space, cytosolOne of 4 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
- 5,6,7,8-tetrahydrofolate:NAD+ oxidoreductase
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (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
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- A + NADH + H(+) = AH2 + NAD(+)
- 3-iodothyronamine + iodide + A + H(+) = 3,5-diiodothyronamine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- A + NADH + H(+) = AH2 + NAD(+)
- 3-iodo-L-thyronine + iodide + A + H(+) = 3,5-diiodo-L-thyronine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 9 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- A + NADH + H(+) = AH2 + NAD(+)
- 3'-iodo-L-thyronine + iodide + A + H(+) = 3',5'-diiodo-L-thyronine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- A + NADH + H(+) = AH2 + NAD(+)
- 3'-iodothyronamine + iodide + A + H(+) = 3',5'-diiodothyronamine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- A + NADH + H(+) = AH2 + NAD(+)
- 3,3'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2
Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 5 routes
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrix
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 2 routes
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 2 routes
Catalysed by FAAHcytosol, extracellular space
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
- dihydrofolate:NAD+ oxidoreductase
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- medium-chain acyl-CoA ligase (hexanoic acid)
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosolOne of 6 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]
Catalysed by ALDH3A2cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
- long-chain-fatty-acid-CoA ligase (EPA)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
- Propanoyl-CoA:acetyl-CoA C-acyltransferase
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, peroxisomeOne of 7 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
- K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)
Catalysed by PTGS2, MOCOS, SLC1A1inner side of the membrane, outer side of the membraneOne of 2 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
- transport of chloride and cysteine (cytosol to extracellular)
Catalysed by PTGS2, MOCOS, SLC6A14extracellular space, cytosolOne of 2 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- (R)-malate + A = oxaloacetate + AH2
- L-Aspartate:2-oxoglutarate aminotransferase
Catalysed by PTGS2, D2HGDH, GOT2mitochondrial matrixOne of 5 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- (R)-malate + A = oxaloacetate + AH2
- acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
Catalysed by PTGS2, D2HGDH, CSmitochondrial matrixOne of 2 routes
- (10Z)-heptadecenoic acid formation
- N-acylsphingosine amidohydrolase
- dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 2 routes
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate
- (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O
- methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate
- (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O
- thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
- De novo synthesis of 2Fe2S
Catalysed by PTGS2, MOCOS, NDUFAB1, FDXR and 5 moremitochondrial matrix
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- alkane 1-monooxygenase (lauric acid)
Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes