Compound

8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate

An icosanoid anion that is the conjugate base of 8,9-EET, obtained by deprotonation of the carboxy group; major species at pH 7.3.

Definition from ChEBI (CHEBI:84025), read 2026-09-23. CC BY 4.0.

CHEBI:84025ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound, anion
Formula: C20H31O3
Mass: 319.465 g/mol
Charge: -1
InChIKey: DBWQSCSXHFNTMO-TYAUOURKSA-M
SMILES: CCCCC/C=CC/C=CCC1OC1C/C=CCCCC(=O)[O-]
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

2 entities

2 entities reached.

0 reported hops2 assembled from the scaffold

What the reference databases state

Statements

5 statements

5 statements · 1 reference database · Subject: 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate · Sources: Human-GEM

Order

(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateCompoundHuman-GEM MAR00946Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateCompoundHuman-GEM MAR00947Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateCompoundHuman-GEM MAR00948Inferred only
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate is metabolised by EPHX1ProteinHuman-GEM MAR00949Inferred only
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate is metabolised by EPHX2ProteinHuman-GEM MAR00949Inferred only

Reactions

12 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 undeterminableGO:0005829, GO:0005777, GO:0005759, GO:0005783, GO:0005634, GO:0005615
Human-GEM MAR00036CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+proton+NADPH(4-)+dioxygen8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+water+NADP(3-)
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 14 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005829
Human-GEM MAR00946CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+FADH2+dioxygen8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+FAD+water
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 14 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005829
Human-GEM MAR00947CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+FADH2+dioxygen8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+FAD+water
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 14 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005783
Human-GEM MAR00948CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+waterMAM01208c
Catalysed by EPHX2 or EPHX1
Reaction pageLeft to rightBalancedEC 3.3.2.9, 3.3.2.10GO:0005829
Human-GEM MAR00949CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate
Reaction pageReversibleBalancedGO:0005829, GO:0005615
Human-GEM MAR10143CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+ATP+water8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+ADP+proton+phosphate(3-)
Reaction pageLeft to rightBalancedGO:0005829, GO:0005615
Human-GEM MAR10144CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR10145CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+waterCHEBI:84032
Catalysed by EPHX1 or EPHX2 or EPHX3
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:44048CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+ATP(4-)+coenzyme A(4-)8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoyl-CoA+AMP+diphosphate(3-)
Catalysed by ACSL4
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:52008CC BY 4.0Reference data
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:137474+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP4F2 or CYP4F3
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53572CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+reduced [NADPH--hemoprotein reductase]+dioxygen8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+oxidized [NADPH--hemoprotein reductase]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:64984CC BY 4.0Reference data

Other names

6 names

Resolves to: 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate

Also called: 8,9-Ep-(5Z,11Z,14Z)-ETrE8,9-EpETE8,9-EpETrE(1-)8,9-EpETrE(1−)8,9-epoxy-(5Z,11Z,14Z)-icosatrienoate
Systematic name: (5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoate