Compound

(12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

An icosanoid anion that is the conjugate base of 12(S)-HETE, obtained by deprotonation of the carboxy group; major species at pH 7.3.

Definition from ChEBI (CHEBI:90680), read 2026-09-23. CC BY 4.0.

CHEBI:90680ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound, anion
Formula: C20H31O3
Mass: 319.465 g/mol
Charge: -1
InChIKey: ZNHVWPKMFKADKW-LQWMCKPYSA-M
SMILES: CCCCC/C=CC[C@H](O)/C=C/C=CC/C=CCCCC(=O)[O-]
Look it up: ChEBI By InChIKey

Identity from ChEBI. 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

Chemical structure

(5S)-hydroperoxy-(12S)-hydroxy-(6E,8Z,10E,14Z)-eicosatetraenoate has the functional parent (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateCompoundChEBI CHEBI:145837Inferred only
(12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is the enantiomer of (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateCompoundChEBI CHEBI:83343Inferred only

Statements

3 statements

3 statements · 1 reference database · Subject: (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate · Sources: Rhea

Order

(12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is converted to (5S)-hydroperoxy-(12S)-hydroxy-(6E,8Z,10E,14Z)-eicosatetraenoateCompoundRhea RHEA:62648Inferred only
(5S)-hydroperoxy-(12S)-hydroxy-(6E,8Z,10E,14Z)-eicosatetraenoate is converted to (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateCompoundRhea RHEA:62648Inferred only
(12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of ALOX5ProteinRhea RHEA:62648Inferred only

Reactions

2 reactions

(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate+2glutathione(12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate+glutathione disulfide+water
Catalysed by GPX1 or GPX4
Reaction pageLeft to rightBalanced
Rhea RHEA:50708CC BY 4.0Reference data
(12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate+dioxygen(5S)-hydroperoxy-(12S)-hydroxy-(6E,8Z,10E,14Z)-eicosatetraenoate
Catalysed by ALOX5
Reaction pageDirection not assertedBalanced
Rhea RHEA:62648CC BY 4.0Reference data

Other names

3 names

Resolves to: (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

Also called: (12S)-H-(5Z,8Z,10E,14Z)-ETE(12S)-HETE
Systematic name: (5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoate