Reaction: CYP monooxygenates EPA to 18(S)-HpEPE

- in pathway: Biosynthesis of E-series 18(S)-resolvins
The same cytochrome P450 (CYP) isoforms that metabolise the ω-6 polyunsaturated fatty acid (PUFA) arachidonic acid (AA) accept the ω-3 PUFAs eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) as efficient alternative substrates (Arnold et al. 2010a). Several human CYPs are thought to oxidise EPA to 18(S)-hydroperoxyeicosapentaenoic acid (18(S)-HpEPE) although the exact CYP enzymes involved are not known (Arnold et al. 2010b, Weylandt et al. 2012). Microbial CYPs can generate 18-HEPE from EPA (Serhan et al. 2000) that can be converted by human PMNs to RvE1 and RvE2 (Arita et al. 2005). The microbial content in the local environment can therefore, also be a critical factor in the production of E-series resolvins in vivo in humans.
Reaction - small molecule participants:
18(S)-HpEPE [cytosol]
NADP+ [cytosol]
EPA [cytosol]
H+ [cytosol]
O2 [cytosol]
NADPH [cytosol]
Reactome.org reaction link: R-HSA-9018874

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Reaction input - small molecules:
all-cis-5,8,11,14,17-icosapentaenoic acid
ChEBI:28364
hydron
ChEBI:15378
dioxygen
ChEBI:15379
NADPH(4-)
ChEBI:57783
Reaction output - small molecules:
(18S)-hydroperoxyicosapentaenoic acid
ChEBI:138387
NADP(3-)
ChEBI:58349
Reactome.org link: R-HSA-9018874