Compound

(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate

An icosanoid anion that is the conjugate base of 18(R)-HEPE arising from deprotonation of the carboxylic acid group; major species at pH 7.3.

Definition from ChEBI (CHEBI:90818), read 2026-09-23. CC BY 4.0.

CHEBI:90818ChEBI

Open in the graph

Structure

2D depiction

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

3 entities

3 entities reached.

0 reported hops3 assembled from the scaffold

What the reference databases state

Chemical structure

(18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is the enantiomer of (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundChEBI CHEBI:132083Inferred only

Statements

7 statements

7 statements · 2 reference databases · Subject: (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate · Sources: Human-GEM, Rhea

Order

(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is converted to (5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:51968Inferred only
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate is converted to (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundHuman-GEM MAR02585Inferred only
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is a substrate of ALOX5ProteinRhea RHEA:51968Inferred only
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is a substrate of ALOX5ProteinHuman-GEM MAR02586Inferred only
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is a substrate of ALOX5ProteinHuman-GEM MAR03900Inferred only
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is transported by ABCC1ProteinHuman-GEM MAR11792Inferred only
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is transported by ABCC4ProteinHuman-GEM MAR11792Inferred only

Reactions

9 reactions

11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoate+15-oxoprostaglandin E1+MAM00014x+(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+MAM00254c+MAM00254m+MAM00254x+20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00274c+MAM00274r+MAM00276c+MAM00277c+MAM00278c+MAM00280c+MAM00282c+11beta-hydroxyandrost-4-ene-3,17-dione+11beta-hydroxyandrost-4-ene-3,17-dione+11beta-hydroxyandrost-4-ene-3,17-dione+MAM00293c+MAM00297c+MAM00298c+MAM00304c+MAM00306c+MAM00308c+MAM00318c+MAM00318r+MAM00319c+MAM00320c+MAM00321c+MAM00322c+MAM00323c+MAM00323r+MAM00324r+MAM00327c+MAM00327r+MAM00328c+MAM00328r+MAM00333r+12-oxo-(5Z,8Z,10E,14Z)-eicosatetraenoate+(13S)-hydroxy-(9Z,11E)-octadecadienoate+MAM00338c+MAM00340c+MAM00352r+13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00364c+14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+(15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate+MAM00378c+MAM00382c+15-deoxy-Delta(12,14)-prostaglandin J2+MAM00384c+MAM00386c+MAM00386r+MAM00386x+MAM00387c+MAM00387r+MAM00387x+MAM00388c+MAM00388r+MAM00388x+MAM00389c+MAM00389r+MAM00389x+15-oxoprostaglandin F2alpha+MAM00395c+16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00398x+17-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00424m+MAM00425x+MAM00426c+18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00430c+MAM00590c+MAM00595c+MAM00595r+MAM00598c+MAM00598r+MAM00602c+MAM00687m+MAM00687x+MAM01038n+MAM01039x+MAM01041n+MAM01046c+MAM01047c+MAM01049c+MAM01050c+MAM01051c+5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+MAM01055c+MAM01120c+MAM01120r+MAM01122c+MAM01122r+MAM01150c+MAM01150m+MAM01150x+MAM01153c+MAM01153m+MAM01153r+MAM01153x+MAM01167c+MAM01168r+MAM01171c+MAM01171m+MAM01171x+MAM01172c+MAM01172m+MAM01172x+7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM01202c+MAM01208c+8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+MAM01210c+MAM01213c+MAM01239c+(11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoate+(11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoate+MAM02368c+MAM02395n+MAM02395r+MAM02395x+MAM02396r+MAM02396x+malonaldehyde+MAM02538c+MAM02538n+MAM02649m+MAM02649x+prostaglandin E2+prostaglandin E3+prostaglandin H1+prostaglandin J2+MAM02797c+MAM02798c+MAM02799c+MAM02851c+MAM02852c+MAM02862c+MAM02863c+MAM02864c+MAM03055c+MAM03055r+MAM03055x+MAM03056cMAM10003e
Reaction pageLeft to rightBalance undeterminablecytosol, peroxisome, mitochondrial matrix, endoplasmic reticulum, nucleus, extracellular space
Human-GEM MAR00036CC BY 4.0Reference data
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate+proton+NADPH(4-)+dioxygen(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+water+NADP(3-)
Catalysed by PTGS2 or PTGS1
Reaction pageLeft to rightBalancedEC 1.14.99.1cytosol
Human-GEM MAR02585CC BY 4.0Reference data
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+dioxygenMAM01056c+water
Catalysed by ALOX5
Reaction pageLeft to rightBalancedEC 1.13.11.34cytosol
Human-GEM MAR02586CC BY 4.0Reference data
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+dioxygenMAM01056n+water
Catalysed by ALOX5
Reaction pageLeft to rightBalancedEC 1.13.11.34nucleus
Human-GEM MAR03900CC BY 4.0Reference data
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+ATP+water(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+ADP+proton+phosphate(3-)
Transported by ABCC1 or ABCC4
Reaction pageLeft to rightBalancedEC 7.6.2.2cytosol, extracellular space
Human-GEM MAR11792CC BY 4.0Reference data
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR11907CC BY 4.0Reference data
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate+AH2+dioxygen(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+A+water
Catalysed by PTGS2
Reaction pageLeft to rightBalanced
Rhea RHEA:48836CC BY 4.0Reference data
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+dioxygenCHEBI:133822
Reaction pageDirection not assertedBalanced
Rhea RHEA:50868CC BY 4.0Reference data
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+dioxygen(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate
Catalysed by ALOX5
Reaction pageLeft to rightBalanced
Rhea RHEA:51968CC BY 4.0Reference data

Where it reaches

3 systems, 6 regions, 9 tissues, 9 transporter routes — routes, not measurements: transporters known to carry (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate are expressed there, and no source reports it arriving.

Loading the model…

Nervous

Digestive

Reproductive

Other names

10 names

Resolves to: (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate

Also called: (18R)-H-(5Z,8Z,11Z,14Z,16E)-EPE(18R)-HEPE(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-icosapentaenoate(1-)(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-icosapentaenoate(1−)(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosapentaenoate18R-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate(1-)18R-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate(1−)18R-hydroxy-eicosapentaenoate18R-hydroxy-icosapentaenoate
Systematic name: (5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoate