Compound

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

Conjugate base of 12(S)-HPETE arising from deprotonation of the carboxylic acid function.

Definition from ChEBI (CHEBI:57444), read 2026-09-23. CC BY 4.0.

CHEBI:57444ChEBI

Open in the graph

Structure

2D depiction · 3D model shown

Loading the model…

A generated conformer of (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H31O4
Mass: 335.464 g/mol
Charge: -1
InChIKey: ZIOZYRSDNLNNNJ-LQWMCKPYSA-M
SMILES: CCCCC/C=CC[C@@H](/C=C/C=CC/C=CCCCC(=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

8 entities

8 entities reached.

0 reported hops8 assembled from the scaffold

What the reference databases state

Statements

15 statements

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

Order

(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is converted to (10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoateCompoundRhea RHEA:37951Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateCompoundRhea RHEA:10428Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is converted to (8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoateCompoundRhea RHEA:37955Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is converted to (8S)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoateCompoundRhea RHEA:50216Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is converted to 12-oxo-(5Z,8Z,10E,14Z)-eicosatetraenoateCompoundRhea RHEA:37947Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is metabolised by CYP1A1ProteinRhea RHEA:37947Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is metabolised by CYP1A2ProteinRhea RHEA:37947Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is metabolised by CYP1B1ProteinRhea RHEA:37947Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is metabolised by CYP2S1ProteinRhea RHEA:37947Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of ALOX15ProteinRhea RHEA:50216Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of ALOXE3ProteinRhea RHEA:37947Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of ALOXE3ProteinRhea RHEA:37955Inferred only

Show the remaining 3

(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of ALOXE3ProteinRhea RHEA:37951Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of GPX1ProteinRhea RHEA:50708Inferred only
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate is a substrate of GPX4ProteinRhea RHEA:50708Inferred only

Reactions

6 reactions

(5Z,8Z,11Z,14Z)-eicosatetraenoate+dioxygen(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
Catalysed by ALOX5 or ALOX15 or ALOX12
Reaction pageLeft to rightBalanced
Rhea RHEA:10428CC BY 4.0Reference data
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate12-oxo-(5Z,8Z,10E,14Z)-eicosatetraenoate+water
Catalysed by CYP1A1 or CYP1A2 or CYP1B1 or CYP2S1 or ALOXE3
Reaction pageLeft to rightBalanced
Rhea RHEA:37947CC BY 4.0Reference data
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoate
Catalysed by ALOXE3
Reaction pageLeft to rightBalanced
Rhea RHEA:37951CC BY 4.0Reference data
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoate
Catalysed by ALOXE3
Reaction pageLeft to rightBalanced
Rhea RHEA:37955CC BY 4.0Reference data
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate(8S)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoate
Catalysed by ALOX15
Reaction pageLeft to rightBalanced
Rhea RHEA:50216CC BY 4.0Reference data
(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

Other names

4 names

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

Also called: (12S)-Hp-(5Z,8Z,10E,14Z)-ETE(12S)-HpETE12(S)-HPETE anion
Systematic name: (5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoate