(5Z,8Z,11Z,14Z)-eicosatetraenoate
362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API
735 compounds within 3 steps: 59 in 1, 173 in 2, 503 in 3
Three steps
- transport of arachidonate (cytosol to extracellular)
- solute carrier organic anion transporter (chenodiol)
- Chenodeoxycholic acid 6alpha-hydroxylase
Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol
- transport of arachidonate (cytosol to extracellular)
- transport of prostaglandin A2 (cytosol to extracellular)
- prostaglandin A2 + glutathione = prostaglandin A2-S-(R)-glutathione
Catalysed by SLCO1B1, GSTA1, GSTM1extracellular space, cytosol
- transport of arachidonate (cytosol to extracellular)
- transport of prostaglandin A2 (cytosol to extracellular)
- prostaglandin A2 + glutathione = prostaglandin A2-S-(S)-glutathione
Catalysed by SLCO1B1, GSTP1, GSTM1extracellular space, cytosol
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + O2 = 14-hydroperoxy-(7Z,10Z,12E,16Z,19Z)-docosapentaenoate
Catalysed by ALOX15cytosol, extracellular space
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
- 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
- N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
Catalysed by PAMcytosolOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular spaceOne of 2 routes
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
Catalysed by PM20D1cytosol, extracellular space
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (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
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (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
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- (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
- transport of arachidonate (cytosol to extracellular)
- solute carrier organic anion transporter (chenodiol)
- chenodeoxycholate + UDP-alpha-D-glucuronate = chenodeoxycholoyl-24-O-(beta-D-glucuronate) + UDP
Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, UGT2A2 and 1 moreextracellular space, cytosol
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
- (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
- (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroxy-(15S)-hydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoate
- transport of arachidonate and GSH (cytosol to extracellular)
- glutathione gamma-glutamylaminopeptidase
- N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate
Catalysed by GGTLC3, GGT1, GGT5, GGTLC2 and 3 moreextracellular space, cytosol
- transport of arachidonate (cytosol to extracellular)
- solute carrier organic anion transporter (chenodiol)
- a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, GBA2extracellular space, cytosolOne of 2 routes
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
- 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
- N-dodecanoylglycine + 2 L-ascorbate + O2 = N-dodecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
Catalysed by PAMcytosolOne of 2 routes
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
- 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
- N-(9Z,12Z,15Z)-octadecatrienoylglycine + 2 L-ascorbate + O2 = N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
Catalysed by PAMcytosol
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
- 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
- N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
Catalysed by PAMcytosolOne of 2 routes
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
- 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
- N-octanoylglycine + 2 L-ascorbate + O2 = N-octanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
Catalysed by PAMcytosolOne of 2 routes
- N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
- N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
- 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)
- transport of arachidonate and GSH (cytosol to extracellular)
- glutathione gamma-glutamylaminopeptidase
- 2 L-cysteinylglycine + [protein]-disulfide = L-cystine-bis-glycine + [protein]-dithiol
Catalysed by GGTLC3, GGT1, GGT5, GGTLC2 and 3 moreextracellular space, cytosolOne of 2 routes
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
- (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O
- (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(12S)-hydroxy-(6E,8Z,10E,14Z)-eicosatetraenoate
- 1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
- 1-octadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
- 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + O2 = 1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphocholine
- (10Z)-heptadecenoic acid formation
- (10Z)-heptadecenoic acid formation
- 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