Compound

1-(9Z-octadecenoyl)-sn-glycero-3-phosphate

A 1-acyl-sn-glycerol 3-phosphate(2−) obtained by deprotonation of the phosphate OH groups of 1-oleoyl-sn-glycero-3-phosphate.

Definition from ChEBI (CHEBI:74544), read 2026-09-23. CC BY 4.0.

CHEBI:74544ChEBI

Open in the graph

Structure

2D depiction

No three-dimensional record for this entry.

Class: Organic compound, anion
Formula: C21H39O7P
Mass: 434.51 g/mol
Charge: -2
InChIKey: WRGQSWVCFNIUNZ-GDCKJWNLSA-L
SMILES: CCCCCCCC/C=CCCCCCCCC(=O)OC[C@@H](O)COP(=O)([O-])[O-]
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

18 entities

18 entities reached.

0 reported hops18 assembled from the scaffold

Show the remaining 6

What the reference databases state

Statements

72 statements

72 statements · 1 reference database · Subject: 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate · Sources: Rhea

Order

1-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine is converted to 1-(9Z-octadecenoyl)-sn-glycero-3-phosphateCompoundRhea RHEA:38931Inferred only
1-(9Z-octadecenoyl)-sn-glycerol is converted to 1-(9Z-octadecenoyl)-sn-glycero-3-phosphateCompoundRhea RHEA:41079Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is converted to 1-(9Z-octadecenoyl)-sn-glycerolCompoundRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is metabolised by EPHX2ProteinRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ABHD5ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ABHD5ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ABHD5ProteinRhea RHEA:37443Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ABHD5ProteinRhea RHEA:37451Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ABHD5ProteinRhea RHEA:37147Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ACP3ProteinRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of ACP6ProteinRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37175Inferred only

Show the remaining 60

1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37171Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:40195Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37607Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37603Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37591Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37147Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37155Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37443Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT1ProteinRhea RHEA:37159Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37171Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37159Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37603Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37155Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT2ProteinRhea RHEA:37175Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37595Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:42592Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37147Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37443Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37159Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37155Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT3ProteinRhea RHEA:37175Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT4ProteinRhea RHEA:55312Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37147Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37155Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37171Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37175Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37443Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:37595Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of AGPAT5ProteinRhea RHEA:42592Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT2ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT2ProteinRhea RHEA:37443Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT3ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT3ProteinRhea RHEA:37159Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT3ProteinRhea RHEA:37147Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT3ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of GPAT3ProteinRhea RHEA:37171Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LCLAT1ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LCLAT1ProteinRhea RHEA:37147Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LCLAT1ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37155Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37171Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37159Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37175Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of LPCAT2ProteinRhea RHEA:37595Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PLPP1ProteinRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PLPP4ProteinRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PLPP5ProteinRhea RHEA:39835Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PNPLA3ProteinRhea RHEA:37143Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PNPLA3ProteinRhea RHEA:37443Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PNPLA3ProteinRhea RHEA:37131Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of PNPLA3ProteinRhea RHEA:37159Inferred only
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate is a substrate of TAFAZZINProteinRhea RHEA:67752Inferred only

Reactions

29 reactions

1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+(9Z)-octadecenoyl-CoA1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT2 or GPAT3 or GPAT2 or LCLAT1 or LPCAT2 or ABHD5 or AGPAT1 or AGPAT3 or PNPLA3 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37131CC BY 4.0Reference data
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+hexadecanoyl-CoA1-(9Z)-octadecenoyl-2-hexadecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT2 or GPAT3 or LCLAT1 or LPCAT2 or ABHD5 or AGPAT1 or PNPLA3
Reaction pageLeft to rightBalanced
Rhea RHEA:37143CC BY 4.0Reference data
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+octadecanoyl-CoA1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by GPAT3 or LCLAT1 or ABHD5 or AGPAT1 or AGPAT3 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37147CC BY 4.0Reference data
heptadecanoyl-CoA+1-(9Z-octadecenoyl)-sn-glycero-3-phosphate1-(9Z)-octadecenoyl-2-heptadecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT2 or LPCAT2 or AGPAT1 or AGPAT3 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37155CC BY 4.0Reference data
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+(9Z,12Z)-octadecadienoyl-CoA1-(9Z)-octadecenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT2 or GPAT3 or LPCAT2 or AGPAT1 or AGPAT3 or PNPLA3
Reaction pageLeft to rightBalanced
Rhea RHEA:37159CC BY 4.0Reference data
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+tetradecanoyl-CoA1-(9Z)-octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT2 or GPAT3 or LPCAT2 or AGPAT1 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37171CC BY 4.0Reference data
pentadecanoyl-CoA+1-(9Z-octadecenoyl)-sn-glycero-3-phosphate1-(9Z)-octadecenoyl-2-pentadecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT2 or LPCAT2 or AGPAT1 or AGPAT3 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37175CC BY 4.0Reference data
sn-glycerol 3-phosphate+(9Z)-octadecenoyl-CoA1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by GPAT3 or GPAT4 or GPAM
Reaction pageLeft to rightBalanced
Rhea RHEA:37199CC BY 4.0Reference data
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+(5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by GPAT2 or ABHD5 or AGPAT1 or AGPAT3 or PNPLA3 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37443CC BY 4.0Reference data
eicosanoyl-CoA+1-(9Z-octadecenoyl)-sn-glycero-3-phosphate1-(9Z)-octadecenoyl-2-eicosanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by ABHD5
Reaction pageLeft to rightBalanced
Rhea RHEA:37451CC BY 4.0Reference data
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate+dodecanoyl-CoA1-(9Z)-octadecenoyl-2-dodecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by AGPAT1
Reaction pageLeft to rightBalanced
Rhea RHEA:37591CC BY 4.0Reference data
nonadecanoyl-CoA+1-(9Z-octadecenoyl)-sn-glycero-3-phosphate1-(9Z)-octadecenoyl-2-nonadecanoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by LPCAT2 or AGPAT3 or AGPAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:37595CC BY 4.0Reference data

Show the remaining 17

Other names

8 names

Resolves to: 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate

Also called: 1-(9Z)-octadecenoyl-sn-glycero-3-phosphate(2-)1-(9Z)-octadecenoyl-sn-glycero-3-phosphate(2−)1-(Z)-octadec-9-enoyl-sn-glycero-3-phosphate(2-)1-(Z)-octadec-9-enoyl-sn-glycero-3-phosphate(2−)1-oleoylglycero-3-phosphate(2-)1-oleoylglycero-3-phosphate(2−)PA(18:1(9Z)/0:0)
Systematic name: (2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphate