Compound

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine

An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.

Definition from ChEBI (CHEBI:2700), read 2026-09-23. CC BY 4.0.

CHEBI:2700ChEBI

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Structure

2D depiction

No three-dimensional record for this entry.

Class: Organic compound
Formula: C22H37NO2
Mass: 347.543 g/mol
Charge: 0
InChIKey: LGEQQWMQCRIYKG-DOFZRALJSA-N
SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)NCCO
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

7 entities

7 entities reached.

0 reported hops7 assembled from the scaffold

What the reference databases state

Chemical structure

2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate has the functional parent N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineCompoundChEBI CHEBI:76070Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine has the functional parent arachidonic acidCompoundChEBI CHEBI:2700Inferred only

Statements

14 statements

14 statements · 1 reference database · Subject: N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine · Sources: Rhea

Order

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2B6ProteinRhea RHEA:53144Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2B6ProteinRhea RHEA:53148Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2B6ProteinRhea RHEA:53140Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2D6ProteinRhea RHEA:53148Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2D6ProteinRhea RHEA:53152Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2D6ProteinRhea RHEA:53144Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP2D6ProteinRhea RHEA:53140Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP3A4ProteinRhea RHEA:53144Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP3A4ProteinRhea RHEA:53140Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP3A4ProteinRhea RHEA:53148Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is metabolised by CYP4X1ProteinRhea RHEA:53148Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is a substrate of FAAHProteinRhea RHEA:26136Inferred only

Show the remaining 2

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is a substrate of FAAH2ProteinRhea RHEA:26136Inferred only
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine is a substrate of PLA2G15ProteinRhea RHEA:38751Inferred only

Reactions

16 reactions

(5Z,8Z,11Z,14Z)-eicosatetraenoate+ethanolamineN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+water
Catalysed by FAAH
Reaction pageLeft to rightBalancedEC 3.5.1.99cytosol
Human-GEM MAR01346CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR10140CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR10213CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+waterethanolamine+(5Z,8Z,11Z,14Z)-eicosatetraenoate
Catalysed by FAAH or FAAH2
Reaction pageLeft to rightBalanced
Rhea RHEA:26136CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate+(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Catalysed by PLA2G15
Reaction pageLeft to rightBalanced
Rhea RHEA:38751CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine+waterN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+sn-glycerol 3-phosphate+hydron
Catalysed by GDE1
Reaction pageLeft to rightBalanced
Rhea RHEA:45428CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+waterN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate+hydron
Catalysed by NAPEPLD
Reaction pageLeft to rightBalanced
Rhea RHEA:45528CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+waterN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+hydron
Catalysed by NAPEPLD or GDPD3 or GDPD1
Reaction pageLeft to rightBalanced
Rhea RHEA:45544CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:136989+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP3A4 or CYP2D6 or CYP2B6
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53140CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:136990+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP3A4 or CYP2D6 or CYP2B6
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53144CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:136991+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP3A4 or CYP2D6 or CYP2B6 or CYP4X1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53148CC BY 4.0Reference data
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:136992+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP2D6
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53152CC BY 4.0Reference data

Show the remaining 4

Other names

20 names

Resolves to: N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine

Also called: (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide(all-Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamideAEAAnandamideAnandamide (20:4, n-6)Anandamide (20.4, N-6)Anandamide(20:4, N-6)Arachidonic acid N-(hydroxyethyl)amidearachidonoyl ethanolamideArachidonoyl-EAarachidonoylethanolamideArachidonylethanolamideN-(2-Hydroxyethyl)anachidonamideN-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamideN-arachidonoyl ethanolamineN-arachidonoyl-2-hydroxyethylamideN-arachidonoylethanolamineNAE (20:4(5Z,8Z,11Z,14Z))NAE 20:4
Systematic name: (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide