Compound

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol

An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.

Definition from ChEBI (CHEBI:52392), read 2026-09-23. CC BY 4.0.

CHEBI:52392ChEBI

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Structure

2D depiction

No three-dimensional record for this entry.

Class: Organic compound
Formula: C23H38O4
Mass: 378.553 g/mol
Charge: 0
InChIKey: RCRCTBLIHCHWDZ-DOFZRALJSA-N
SMILES: [H]C(CO)(CO)OC(=O)CCC/C=CC/C=CC/C=CC/C=CCCCCC
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

26 entities

26 entities reached.

0 reported hops26 assembled from the scaffold

Show the remaining 14

What the reference databases state

Chemical structure

2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerol has the functional parent 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolCompoundChEBI CHEBI:146254Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol has the functional parent arachidonic acidCompoundChEBI CHEBI:52392Inferred only

Statements

43 statements

43 statements · 2 reference databases · Subject: 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol · Sources: Human-GEM, Rhea

Order

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolCompoundHuman-GEM MAR03012Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateCompoundHuman-GEM MAR03012Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateCompoundHuman-GEM MAR03010Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateCompoundRhea RHEA:43316Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateCompoundHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolCompoundHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is converted to 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolCompoundHuman-GEM MAR03010Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerolCompoundRhea RHEA:63224Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerolCompoundRhea RHEA:53332Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is converted to 2-glyceryl-prostaglandin G2CompoundRhea RHEA:45288Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is metabolised by CES1ProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is metabolised by CES2ProteinRhea RHEA:26132Inferred only

Show the remaining 31

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is metabolised by EPHX1ProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of ABHD12ProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of ABHD16AProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of ABHD2ProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of ABHD6ProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of AGKProteinRhea RHEA:43316Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of ALOX15BProteinRhea RHEA:63224Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of ALOX15BProteinRhea RHEA:53332Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of FAAHProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of FAAHProteinHuman-GEM MAR01347Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of LIPEProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of LPIN1ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of LPIN2ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of LPIN3ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of MGLLProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP1ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP2ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP3ProteinHuman-GEM MAR03012Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP3ProteinHuman-GEM MAR03010Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP3ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP4ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPP5ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPPR2ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPPR3ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PLPPR4ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PNPLA6ProteinRhea RHEA:26132Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PTGS1ProteinHuman-GEM MAR03006Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PTGS1ProteinHuman-GEM MAR01350Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PTGS2ProteinHuman-GEM MAR03006Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PTGS2ProteinRhea RHEA:45288Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol is a substrate of PTGS2ProteinHuman-GEM MAR01350Inferred only

Reactions

16 reactions

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+water(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM01983c+proton
Catalysed by FAAH
Reaction pageReversibleBalancedEC 3.5.1.99cytosol
Human-GEM MAR01347CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+dioxygenMAM00322c
Catalysed by PTGS2 or PTGS1
Reaction pageLeft to rightBalancedEC 1.14.99.1cytosol
Human-GEM MAR01350CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+phosphate(3-)
Catalysed by PLPP1 or LPIN2 or PLPPR2 or PLPPR4 or PLPPR3 or LPIN3 or LPIN1 or PLPP2 or PLPP5 or PLPP3 or PLPP4
Reaction pageReversibleBalancedEC 3.1.3.4cytosol
Human-GEM MAR01352CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+dioxygenMAM00322r
Catalysed by PTGS2 or PTGS1
Reaction pageLeft to rightBalancedEC 1.14.99.1endoplasmic reticulum
Human-GEM MAR03006CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+phosphate(3-)
Catalysed by PLPP3
Reaction pageReversibleBalancedEC 3.1.3.4Golgi apparatus
Human-GEM MAR03010CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+phosphate(3-)
Catalysed by PLPP3
Reaction pageReversibleBalancedEC 3.1.3.4endoplasmic reticulum
Human-GEM MAR03012CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR11963CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR13031CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+waterglycerol+(5Z,8Z,11Z,14Z)-eicosatetraenoate+hydron
Catalysed by FAAH or CES2 or ABHD16A or EPHX1 or ABHD2 or CES1 or LIPE or PNPLA6 or ABHD12 or MGLL or ABHD6
Reaction pageLeft to rightBalanced
Rhea RHEA:26132CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+octadecanoate+hydron
Catalysed by DAGLB or ABHD11 or DAGLA
Reaction pageLeft to rightBalanced
Rhea RHEA:38507CC BY 4.0Reference data
1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+(9Z)-octadecenoate+hydron
Catalysed by DAGLB or DAGLA
Reaction pageLeft to rightBalanced
Rhea RHEA:38515CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol+ATP(4-)2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+ADP(3-)+hydron
Catalysed by AGK
Reaction pageLeft to rightBalanced
Rhea RHEA:43316CC BY 4.0Reference data

Show the remaining 4

Other names

13 names

Resolves to: 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol

Also called: 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol2-(5Z,8Z,11Z,14Z)-eicosatetraenoylglycerol2-AG2-Ara-Gl2-Arachidonoyl-glycerol2-Arachidonoylglycerol2-Arachidonyl-glycerol2-ArachidonylglycerolMG 0:0/20:4(5Z,8Z,11Z,14Z)/0:0MG 20:4MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)MG(20:4)
Systematic name: 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate