Compound

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate

A 2-acyl-sn-glycero-3-phosphate(2−) obtained by deprotonation of the phosphate OH groups of 2-arachidonoyl-sn-glycero-3-phosphate; major species at pH 7.3.

Definition from ChEBI (CHEBI:78209), read 2026-09-23. CC BY 4.0.

CHEBI:78209ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound, anion
Formula: C23H37O7P
Mass: 456.516 g/mol
Charge: -2
InChIKey: BDCFJMBXZCIVRH-NZRYSPDRSA-L
SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O[C@H](CO)COP(=O)([O-])[O-]
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

11 entities

11 entities reached.

0 reported hops11 assembled from the scaffold

What the reference databases state

Chemical structure

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate has the functional parent (5Z,8Z,11Z,14Z)-eicosatetraenoateCompoundChEBI CHEBI:78209Inferred only

Statements

20 statements

20 statements · 2 reference databases · Subject: 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate · Sources: Human-GEM, Rhea

Order

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)-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)-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 MAR01352Inferred 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-phosphateCompoundHuman-GEM MAR03012Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of LPIN1ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of LPIN2ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of LPIN3ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP1ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP2ProteinHuman-GEM MAR01352Inferred only

Show the remaining 8

2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP3ProteinHuman-GEM MAR03010Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP3ProteinHuman-GEM MAR03012Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP3ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP4ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPP5ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPPR2ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPPR3ProteinHuman-GEM MAR01352Inferred only
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLPPR4ProteinHuman-GEM MAR01352Inferred only

Reactions

8 reactions

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)-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-sn-glycero-3-phosphocholine+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+choline+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:41392CC 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
a 1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+a fatty acid+hydron
Catalysed by DDHD1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:73975CC BY 4.0Reference data
1,2-di-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+(5Z,8Z,11Z,14Z)-eicosatetraenoate+hydron
Catalysed by DDHD1
Reaction pageLeft to rightBalanced
Rhea RHEA:74159CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+octadecanoate+hydron
Catalysed by DDHD1
Reaction pageLeft to rightBalanced
Rhea RHEA:74163CC BY 4.0Reference data

Other names

4 names

Resolves to: 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate

Also called: 2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphate(2-)2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphate(2−)PA(0:0/20:4(5Z,8Z,11Z,14Z))
Systematic name: (2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphate