Compound

(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

Conjugate base of 15(S)-HPETE arising from deprotonation of the carboxylic acid function.

Definition from ChEBI (CHEBI:57446), read 2026-09-23. CC BY 4.0.

CHEBI:57446ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-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: BFWYTORDSFIVKP-VAEKSGALSA-M
SMILES: CCCCC[C@@H](/C=C/C=CC/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

13 entities

13 entities reached.

0 reported hops13 assembled from the scaffold

Show the remaining 1

CYP2S1ProteinUNIPROT:Q96SQ9metabolized byInferred only11 paths11 endpoints

What the reference databases state

Chemical structure

(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is the enantiomer of (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateCompoundChEBI CHEBI:57446Inferred only

Statements

24 statements

24 statements · 1 reference database · Subject: (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate · Sources: Rhea

Order

(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is converted to (13R)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateCompoundRhea RHEA:37959Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is converted to (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateCompoundRhea RHEA:53400Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is converted to (14S,15S)-epoxy-(5Z,8Z,10E,12E)-eicosatetraenoateCompoundRhea RHEA:50140Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateCompoundRhea RHEA:16869Inferred only
(8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate is converted to (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateCompoundRhea RHEA:50972Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is converted to (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateCompoundRhea RHEA:50972Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is converted to 15-oxo-(5Z,8Z,11Z,13E)-eicosatetraenoateCompoundRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is metabolised by CYP1A1ProteinRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is metabolised by CYP1A2ProteinRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is metabolised by CYP1B1ProteinRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is metabolised by CYP2J2ProteinRhea RHEA:53400Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is metabolised by CYP2J2ProteinRhea RHEA:37959Inferred only

Show the remaining 12

(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is metabolised by CYP2S1ProteinRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of ALOX15ProteinRhea RHEA:50140Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of ALOXE3ProteinRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of ALOXE3ProteinRhea RHEA:37959Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of GPX1ProteinRhea RHEA:76695Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of GPX2ProteinRhea RHEA:76695Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of GPX4ProteinRhea RHEA:76695Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of PTGISProteinRhea RHEA:48856Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of PTGISProteinRhea RHEA:48636Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of PTGS2ProteinRhea RHEA:48856Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of TBXAS1ProteinRhea RHEA:48856Inferred only
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate is a substrate of TBXAS1ProteinRhea RHEA:48636Inferred only

Reactions

8 reactions

(5Z,8Z,11Z,14Z)-eicosatetraenoate+dioxygen(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by ALOX15B or ALOX15 or ALOX12
Reaction pageLeft to rightBalanced
Rhea RHEA:16869CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate(13R)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate
Catalysed by CYP2J2 or ALOXE3
Reaction pageLeft to rightBalanced
Rhea RHEA:37959CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate15-oxo-(5Z,8Z,11Z,13E)-eicosatetraenoate+water
Catalysed by CYP1A1 or CYP1A2 or TBXAS1 or PTGIS or CYP1B1 or CYP2S1 or ALOXE3
Reaction pageLeft to rightBalanced
Rhea RHEA:48636CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate+AH2(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate+A+water
Catalysed by TBXAS1 or PTGS2 or PTGIS
Reaction pageLeft to rightBalanced
Rhea RHEA:48856CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate(14S,15S)-epoxy-(5Z,8Z,10E,12E)-eicosatetraenoate+water
Catalysed by ALOX15
Reaction pageLeft to rightBalanced
Rhea RHEA:50140CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate+dioxygen(8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate
Reaction pageDirection not assertedBalanced
Rhea RHEA:50972CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate(13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate
Catalysed by CYP2J2
Reaction pageLeft to rightBalanced
Rhea RHEA:53400CC BY 4.0Reference data
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate+2glutathione(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate+glutathione disulfide+water
Catalysed by GPX1 or GPX2 or GPX4
Reaction pageLeft to rightBalanced
Rhea RHEA:76695CC BY 4.0Reference data

Other names

4 names

Resolves to: (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

Also called: (15S)-Hp-(5Z,8Z,11Z,13E)-ETE(15S)-HpETE15(S)-HPETE anion
Systematic name: (5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate