Compound

(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate

An icosanoid anion that is the conjugate base of 15(R)-HEPE arising from deprotonation of the carboxylic acid group; major species at pH 7.3.

Definition from ChEBI (CHEBI:90819), read 2026-09-23. CC BY 4.0.

CHEBI:90819ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound, anion
Formula: C20H29O3
Mass: 317.449 g/mol
Charge: -1
InChIKey: WLKCSMCLEKGITB-MXTKCVSJSA-M
SMILES: CC/C=CC[C@@H](O)/C=C/C=CC/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

PTGS2ProteinUNIPROT:P35354substrate ofInferred only56 paths56 endpoints

What the reference databases state

Chemical structure

(15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate is the enantiomer of (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateCompoundChEBI CHEBI:132087Inferred only

Statements

1 statement

1 statement · 1 reference database · Subject: (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate · Sources: Rhea

Order

(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate is a substrate of PTGS2ProteinRhea RHEA:48840Inferred only

Reactions

4 reactions

MAM00373c+ATP+water(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate+ADP+proton+phosphate(3-)
Reaction pageLeft to rightBalancedEC 3.1.2.2GO:0005829, GO:0005615
Human-GEM MAR11829CC BY 4.0Reference data
(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR11830CC BY 4.0Reference data
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate+AH2+dioxygen(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate+A+water
Catalysed by PTGS2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:48840CC BY 4.0Reference data
(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate+dioxygenCHEBI:133821
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:50872CC BY 4.0Reference data

Other names

6 names

Resolves to: (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate

Also called: (15R)-H-(5Z,8Z,11Z,13E,17Z)-EPE(15R)-HEPE(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-icosapentaenoate(15R)-hydroxyeicosapentaenoate(5Z,8Z,11Z,13E,15R,17Z)-15-hydroxyicosapentaenoate
Systematic name: (5Z,8Z,11Z,13E,15R,17Z)-15-hydroxyicosa-5,8,11,13,17-pentaenoate