Compound

(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

A hydroperoxyicosapentaenoate that is the conjugate base of (5S)-HpEPE, arising from deprotonation of the carboxylic acid function; major species at pH 7.3.

Definition from ChEBI (CHEBI:195399), read 2026-09-23. CC BY 4.0.

CHEBI:195399ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H29O4
Mass: 333.448 g/mol
Charge: -1
InChIKey: NKXYOIJDQPQELO-GHWNLOBHSA-M
SMILES: CC/C=CC/C=CC/C=CC/C=CC=C[C@H](CCCC(=O)[O-])OO
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

3 entities

3 entities reached.

0 reported hops3 assembled from the scaffold

What the reference databases state

Statements

5 statements

5 statements · 1 reference database · Subject: (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate · Sources: Rhea

Order

(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate is converted to (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateCompoundRhea RHEA:62600Inferred only
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate is converted to leukotriene A5CompoundRhea RHEA:85591Inferred only
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate is a substrate of ALOX5ProteinRhea RHEA:85591Inferred only
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate is a substrate of GPX1ProteinRhea RHEA:76699Inferred only
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate is a substrate of GPX4ProteinRhea RHEA:76699Inferred only

Reactions

3 reactions

(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate+dioxygen(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate
Catalysed by ALOX5
Reaction pageLeft to rightBalanced
Rhea RHEA:62600CC BY 4.0Reference data
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate+2glutathione(5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate+glutathione disulfide+water
Catalysed by GPX1 or GPX4
Reaction pageLeft to rightBalanced
Rhea RHEA:76699CC BY 4.0Reference data
(5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateleukotriene A5+water
Catalysed by ALOX5
Reaction pageLeft to rightBalanced
Rhea RHEA:85591CC BY 4.0Reference data