Compound

(5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate

A 5(),6(S)-epoxy-18-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoate in which the 12-hydroxy group has S-configuration.

Definition from ChEBI (CHEBI:134661), read 2026-09-23. CC BY 4.0.

CHEBI:134661ChEBI

Open in the graph

Structure

2D depiction · 3D model shown

Loading the model…

A generated conformer of (5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H27O4
Mass: 331.432 g/mol
Charge: -1
InChIKey: ZPAJZAMPZXISSE-FQNQZZNVSA-M
SMILES: CC[C@H](O)/C=C/C=CC/C=CC=CC=C[C@@H]1O[C@H]1CCCC(=O)[O-]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

1 entity

1 entities reached.

0 reported hops1 assembled from the scaffold

ALOX5ProteinUNIPROT:P09917substrate ofInferred only55 paths55 endpoints

What the reference databases state

Statements

3 statements

3 statements · 1 reference database · Subject: (5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate · Sources: Rhea

Order

(5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate is converted to (5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:39107Inferred only
(5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate is converted to (5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:39107Inferred only
(5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate is a substrate of ALOX5ProteinRhea RHEA:39107Inferred only

Reactions

2 reactions

(5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate(5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate+water
Catalysed by ALOX5
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:39107CC BY 4.0Reference data
(5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate+waterCHEBI:136057
Catalysed by LTA4H
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:51988CC BY 4.0Reference data

Other names

1 name

Resolves to: (5S,6S)-epoxy-(18S)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate

Systematic name: 4-{(2S,3S)-3-[(1E,3E,5Z,8Z,10E,12S)-12-hydroxytetradeca-1,3,5,8,10-pentaen-1-yl]oxiran-2-yl}butanoate