Compound

2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine

A 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion obtained by transfer of a proton from the phosphate to the amino group of 2-linoleoyl-sn-glycero-3-phosphoethanolamine; major species at pH 7.3.

Definition from ChEBI (CHEBI:76090), read 2026-09-23. CC BY 4.0.

CHEBI:76090ChEBI

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Structure

2D depiction

Class: Organic compound
Formula: C23H44NO7P
Mass: 477.579 g/mol
Charge: 0
InChIKey: SVRBKLJIDJHADS-USWSLJGRSA-N
SMILES: CCCCC/C=CC/C=CCCCCCCCC(=O)O[C@H](CO)COP(=O)([O-])OCC[NH3+]
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

Chemical structure

2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine has the functional parent linoleic acidCompoundChEBI CHEBI:76090Inferred only

Statements

6 statements

6 statements · 2 reference databases · Subject: 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine · Sources: Human-GEM, Rhea

Order

2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine is a substrate of PLA2G15ProteinRhea RHEA:38831Inferred only
2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine is a substrate of PLAAT2ProteinRhea RHEA:45164Inferred only
2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine is a substrate of PLAAT3ProteinRhea RHEA:45164Inferred only
2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine is a substrate of PLAAT4ProteinRhea RHEA:45164Inferred only
2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine is transported by ATP11AProteinHuman-GEM MAR11621Inferred only
2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine is transported by ATP11CProteinHuman-GEM MAR11621Inferred only

Reactions

5 reactions

2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR10311CC BY 4.0Reference data
ATP+water+2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamineADP+proton+phosphate(3-)+2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine
Transported by ATP11A or ATP11C
Reaction pageLeft to rightBalancedEC 7.6.2.1GO:0005829, GO:0005615
Human-GEM MAR11621CC BY 4.0Reference data
2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine
Reaction pageLeft to rightBalancedEC 7.6.2.2, 7.6.2.1GO:0005615, GO:0005829
Human-GEM MAR11688CC BY 4.0Reference data
1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine+N-(acetyl)-sphing-4-enine2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine+1-hexadecanoyl-N-(acetyl)-sphing-4-enine
Catalysed by PLA2G15
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:38831CC BY 4.0Reference data
1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine+water2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine+hexadecanoate+hydron
Catalysed by PLAAT3 or PLAAT2 or PLAAT4
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:45164CC BY 4.0Reference data

Where it reaches

4 systems, 4 regions, 8 tissues, 8 transporter routes — routes, not measurements: transporters known to carry 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine are expressed there, and no source reports it arriving.

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Nervous

Respiratory

Cardiovascular

Reproductive

Other names

9 names

Resolves to: 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine

Also called: 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine2-linoleoyllysophosphatidylethanolamine zwitterionLPE 18:2LPE(18:2)LPE[0:0/18:2(omega-6)] zwitterionLPE[0:0/18:2(ω-6)] zwitterionPE 0:0/18:2(9Z,12Z)PE(0:0/18:2(9Z,12Z))
Systematic name: 2-azaniumylethyl (2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphate