Compound

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

A 1-acyl-2-arachidonoyl-sn-glycerol 3-phosphate(2−) obtained by deprotonation of the phosphate OH groups of 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphate; major species at pH 7.3.

Definition from ChEBI (CHEBI:77091), read 2026-09-23. CC BY 4.0.

CHEBI:77091ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound, anion
Formula: C41H71O8P
Mass: 722.985 g/mol
Charge: -2
InChIKey: AXJKOPKPNZMCIN-GSEBOFAUSA-L
SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)([O-])[O-]
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

5 entities

5 entities reached.

0 reported hops5 assembled from the scaffold

What the reference databases state

Statements

8 statements

8 statements · 1 reference database · Subject: 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate · Sources: Rhea

Order

1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is converted to 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-cytidine-5'-diphosphateCompoundRhea RHEA:45648Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is converted to 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolCompoundRhea RHEA:43292Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol is converted to 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateCompoundRhea RHEA:40323Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of CDS1ProteinRhea RHEA:45648Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of CDS2ProteinRhea RHEA:45648Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of DDHD1ProteinRhea RHEA:74163Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of LPIN1ProteinRhea RHEA:43292Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate is a substrate of PLA2G4AProteinRhea RHEA:40451Inferred only

Reactions

6 reactions

1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol+ATP(4-)1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+ADP(3-)+hydron
Catalysed by DGKI or DGKA or DGKG or DGKE or DGKQ or DGKZ or DGKD or DGKB
Reaction pageLeft to rightBalanced
Rhea RHEA:40323CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+water1-octadecanoyl-sn-glycero-3-phosphate+(5Z,8Z,11Z,14Z)-eicosatetraenoate+hydron
Catalysed by PLA2G4A
Reaction pageLeft to rightBalanced
Rhea RHEA:40451CC BY 4.0Reference data
1-octadecanoyl-sn-glycero-3-phosphate+(5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT3
Reaction pageLeft to rightBalanced
Rhea RHEA:42588CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+water1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol+hydrogenphosphate
Catalysed by LPIN1
Reaction pageLeft to rightBalanced
Rhea RHEA:43292CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+CTP+hydron1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-cytidine-5'-diphosphate+diphosphate(3-)
Catalysed by CDS2 or CDS1
Reaction pageLeft to rightBalanced
Rhea RHEA:45648CC 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

9 names

Resolves to: 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate

Also called: (2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(stearoyloxy)propyl phosphate1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate(2-)1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate(2−)1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphate(2-)1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphate(2−)PA 18:0/20:4(omega-6)(2-)PA 18:0/20:4(ω-6)(2−)PA(18:0/20:4(5Z,8Z,11Z,14Z))
Systematic name: (2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propyl phosphate