Compound

5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate

An EET(1−) that is the conjugate base of 5,6-EET, obtained by deprotonation of the carboxy group; major species at pH 7.3.

Definition from ChEBI (CHEBI:131992), read 2026-09-23. CC BY 4.0.

CHEBI:131992ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H31O3
Mass: 319.465 g/mol
Charge: -1
InChIKey: VBQNSZQZRAGRIX-QNEBEIHSSA-M
SMILES: CCCCC/C=CC/C=CC/C=CCC1OC1CCCC(=O)[O-]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. 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

Statements

6 statements

6 statements · 2 reference databases · Subject: 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate · Sources: Human-GEM, Rhea

Order

(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoateCompoundHuman-GEM MAR00942Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoateCompoundHuman-GEM MAR00943Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoateCompoundHuman-GEM MAR00944Inferred only
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate is metabolised by CYP2J2ProteinRhea RHEA:49936Inferred only
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate is metabolised by EPHX1ProteinHuman-GEM MAR00945Inferred only
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate is metabolised by EPHX2ProteinHuman-GEM MAR00945Inferred only

Reactions

10 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-)+dioxygen5,6-epoxy-(8Z,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 MAR00942CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+FADH2+dioxygen5,6-epoxy-(8Z,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 MAR00943CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+FADH2+dioxygen5,6-epoxy-(8Z,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 MAR00944CC BY 4.0Reference data
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+waterMAM01051c
Catalysed by EPHX2 or EPHX1
Reaction pageLeft to rightBalancedEC 3.3.2.9, 3.3.2.10GO:0005829
Human-GEM MAR00945CC BY 4.0Reference data
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+ATP+water5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+ADP+proton+phosphate(3-)
Reaction pageLeft to rightBalancedGO:0005829, GO:0005615
Human-GEM MAR10141CC BY 4.0Reference data
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate
Reaction pageReversibleBalancedGO:0005829, GO:0005615
Human-GEM MAR10142CC BY 4.0Reference data
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR10214CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+reduced [NADPH--hemoprotein reductase]+dioxygen5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP2J2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:49936CC BY 4.0Reference data
5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+ATP(4-)+coenzyme A(4-)5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoyl-CoA+AMP+diphosphate(3-)
Catalysed by ACSL4
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:52088CC BY 4.0Reference data

Other names

4 names

Resolves to: 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate

Also called: 5,6-Ep-(8Z,11Z,14Z)-ETrE5,6-EpETrE5,6-epoxy-(8Z,11Z,14Z)-icosatrienoate
Systematic name: 4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoate