(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O

Catalysed by PTGS2One of 5 routes

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O

Catalysed by PTGS2

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

Catalysed by PTGS2

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + 2 O2 = prostaglandin G3

Catalysed by PTGS2

1. (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 CYP2C9

1. (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, CYP2C9

1. (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, CYP2C9

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

Catalysed by ALOX5

1. (10Z)-heptadecenoic acid formation

No catalyst recordedcytosolOne of 4 routes

1. long-chain-fatty-acid-CoA ligase (EPA)

Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosolOne of 3 routes

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

Catalysed by CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 3 more

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (17S,18R)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

Catalysed by CYP2C8, CYP2D6, CYP2J2

1. EPA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate[r]

Catalysed by CYP2E1endoplasmic reticulumOne of 3 routes

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

Catalysed by CYP4F2, CYP4F3, CYP4V2

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoate

Catalysed by ALOX12B

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate

Catalysed by ALOX12

1. prostaglandin-endoperoxide synthase (EPA)

Catalysed by PTGS1, PTGS2cytosolOne of 2 routes

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

Catalysed by PTGS2

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

Catalysed by PTGS2

1. long-chain-fatty-acid-CoA ligase (EPA)
2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase

Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 10 routes

1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
2. (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate

Catalysed by PTGS2, ALOX5