Compound
1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate
A 1-acyl-sn-glycerol 3-phosphate(2−) obtained by deprotonation of the phosphate OH groups of 1-linoleoyl-sn-glycero-3-phosphate.
Definition from ChEBI (CHEBI:74547), read 2026-09-23. CC BY 4.0.
Structure
No three-dimensional record for this entry.
- Class
- Organic compound, anion
- Formula
- C21H37O7P
- Mass
- 432.494 g/mol
- Charge
- -2
- InChIKey
- ZQTAMPRZFOOEEP-KKFOGOCZSA-L
- SMILES
- CCCCC/C=CC/C=CCCCCCCCC(=O)OC[C@@H](O)COP(=O)([O-])[O-]
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
1 entity
1 entities reached.
0 reported hops1 assembled from the scaffold
What the reference databases state
Statements
1 statement
1 statement · 1 reference database · Subject: 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate · Sources: Rhea
- 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate is a substrate of LCLAT1ProteinRhea RHEA:37135Inferred only
Reactions
12 reactions
(9Z,12Z)-octadecadienoyl-CoA+CHEBI:159781-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+CHEBI:1146900
Catalysed by GPAM or GPAT3 or GPAT4 or GPAT2
Reaction pageLeft to rightBalancedEC 2.3.1.15cytosol
Human-GEM MAR00534CC BY 4.0Reference data
0.0001MAM00436c+0.0001MAM00437c+0.0001MAM00438c+0.0001MAM00439c+0.0001MAM00440c+0.0001MAM00441c+0.0001MAM00442c+0.0001MAM00443c+0.0001MAM00444c+0.0001MAM00445c+0.0001MAM00446c+0.0001MAM00447c+0.0001MAM00448c+0.0001MAM00449c+0.0005MAM00450c+0.0001MAM00451c+0.0013MAM00452c+0.0001MAM00453c+0.0001MAM00454c+0.0001MAM00455c+0.0001MAM00456c+0.0028MAM00457c+0.0001MAM00458c+0.0017MAM00459c+0.0001MAM00460c+0.0286MAM00461c+0.0001MAM00462c+0.0001MAM00463c+0.0001MAM00464c+0.0001MAM00465c+0.0001MAM00466c+0.0001MAM00467c+0.0001MAM00468c+0.0001MAM00469c+0.0001MAM00470c+0.0001MAM00471c+0.00241-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0208MAM00474c+0.0013MAM00476c+0.0001MAM00477c+0.0001MAM00478c+0.0048MAM00479c+0.0001MAM00480c+0.0001MAM00481c+0.0001MAM00482c+0.0001MAM00483c+0.00011-dodecanoyl-sn-glycerol 3-phosphate+0.07411-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0037MAM00492c+0.00961-tetradecanoyl-sn-glycerol 3-phosphate+0.0001MAM00494c+0.122MAM00495c+0.641-hexadecanoyl-sn-glycero-3-phosphate+0.0001MAM00497c+0.0001MAM00498c+0.0821-octadecanoyl-sn-glycero-3-phosphate+0.0001MAM00500c+0.0001MAM00501c+0.0001MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00555CC BY 4.0Reference data
0.0005MAM00436c+0.0005MAM00437c+0.0005MAM00438c+0.0005MAM00439c+0.0005MAM00440c+0.0005MAM00441c+0.0005MAM00442c+0.0005MAM00443c+0.0005MAM00444c+0.0005MAM00445c+0.0005MAM00446c+0.0005MAM00447c+0.0005MAM00448c+0.0005MAM00449c+0.0252MAM00450c+0.0039MAM00451c+0.0109MAM00452c+0.0005MAM00453c+0.0005MAM00454c+0.0005MAM00455c+0.0005MAM00456c+0.0026MAM00457c+0.0005MAM00458c+0.0056MAM00459c+0.0011MAM00460c+0.0105MAM00461c+0.0005MAM00462c+0.0005MAM00463c+0.0178MAM00464c+0.0005MAM00465c+0.0005MAM00466c+0.0005MAM00467c+0.0005MAM00468c+0.0005MAM00469c+0.0005MAM00470c+0.0005MAM00471c+0.07091-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0271MAM00474c+0.0228MAM00476c+0.0005MAM00477c+0.0005MAM00478c+0.0036MAM00479c+0.0005MAM00480c+0.0005MAM00481c+0.0005MAM00482c+0.0005MAM00483c+0.00051-dodecanoyl-sn-glycerol 3-phosphate+0.24791-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0047MAM00492c+0.00541-tetradecanoyl-sn-glycerol 3-phosphate+0.0005MAM00494c+0.1143MAM00495c+0.27811-hexadecanoyl-sn-glycero-3-phosphate+0.0005MAM00497c+0.0005MAM00498c+0.12711-octadecanoyl-sn-glycero-3-phosphate+0.0005MAM00500c+0.0005MAM00501c+0.0005MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00556CC BY 4.0Reference data
0.0005MAM00436c+0.0005MAM00437c+0.0005MAM00438c+0.0005MAM00439c+0.0005MAM00440c+0.0005MAM00441c+0.0005MAM00442c+0.0005MAM00443c+0.0005MAM00444c+0.0005MAM00445c+0.0005MAM00446c+0.0005MAM00447c+0.0005MAM00448c+0.0005MAM00449c+0.0459MAM00450c+0.0052MAM00451c+0.0221MAM00452c+0.0005MAM00453c+0.0005MAM00454c+0.0005MAM00455c+0.0005MAM00456c+0.0025MAM00457c+0.0005MAM00458c+0.0067MAM00459c+0.0007MAM00460c+0.0327MAM00461c+0.0005MAM00462c+0.0005MAM00463c+0.0163MAM00464c+0.0005MAM00465c+0.0005MAM00466c+0.0005MAM00467c+0.0005MAM00468c+0.0005MAM00469c+0.0005MAM00470c+0.0005MAM00471c+0.21251-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0285MAM00474c+0.0411MAM00476c+0.0005MAM00477c+0.0005MAM00478c+0.0011MAM00479c+0.0005MAM00480c+0.0005MAM00481c+0.0005MAM00482c+0.0005MAM00483c+0.00051-dodecanoyl-sn-glycerol 3-phosphate+0.13121-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0166MAM00492c+0.03191-tetradecanoyl-sn-glycerol 3-phosphate+0.0005MAM00494c+0.0619MAM00495c+0.12431-hexadecanoyl-sn-glycero-3-phosphate+0.0005MAM00497c+0.0005MAM00498c+0.19831-octadecanoyl-sn-glycero-3-phosphate+0.0005MAM00500c+0.0005MAM00501c+0.0005MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00557CC BY 4.0Reference data
0.0005MAM00436c+0.0005MAM00437c+0.0005MAM00438c+0.0005MAM00439c+0.0005MAM00440c+0.0005MAM00441c+0.0005MAM00442c+0.0005MAM00443c+0.0005MAM00444c+0.0005MAM00445c+0.0005MAM00446c+0.0005MAM00447c+0.0005MAM00448c+0.0005MAM00449c+0.0931MAM00450c+0.0055MAM00451c+0.0286MAM00452c+0.0005MAM00453c+0.0005MAM00454c+0.0005MAM00455c+0.0005MAM00456c+0.0025MAM00457c+0.0005MAM00458c+0.0329MAM00459c+0.0043MAM00460c+0.0058MAM00461c+0.0005MAM00462c+0.0005MAM00463c+0.0174MAM00464c+0.0005MAM00465c+0.0005MAM00466c+0.0005MAM00467c+0.0005MAM00468c+0.0005MAM00469c+0.0005MAM00470c+0.0005MAM00471c+0.20051-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0131MAM00474c+0.0089MAM00476c+0.0005MAM00477c+0.0005MAM00478c+0.0011MAM00479c+0.0005MAM00480c+0.0005MAM00481c+0.0005MAM00482c+0.0005MAM00483c+0.00051-dodecanoyl-sn-glycerol 3-phosphate+0.01771-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0035MAM00492c+0.00551-tetradecanoyl-sn-glycerol 3-phosphate+0.0005MAM00494c+0.0323MAM00495c+0.03371-hexadecanoyl-sn-glycero-3-phosphate+0.0005MAM00497c+0.0005MAM00498c+0.47311-octadecanoyl-sn-glycero-3-phosphate+0.0005MAM00500c+0.0005MAM00501c+0.0005MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00558CC BY 4.0Reference data
0.0005MAM00436c+0.0005MAM00437c+0.0005MAM00438c+0.0005MAM00439c+0.0005MAM00440c+0.0005MAM00441c+0.0005MAM00442c+0.0005MAM00443c+0.0005MAM00444c+0.0005MAM00445c+0.0005MAM00446c+0.0005MAM00447c+0.0005MAM00448c+0.0005MAM00449c+0.0269MAM00450c+0.0124MAM00451c+0.0043MAM00452c+0.0005MAM00453c+0.0005MAM00454c+0.0005MAM00455c+0.0005MAM00456c+0.0027MAM00457c+0.0005MAM00458c+0.0101MAM00459c+0.0031MAM00460c+0.0053MAM00461c+0.0005MAM00462c+0.0005MAM00463c+0.0179MAM00464c+0.0005MAM00465c+0.0005MAM00466c+0.0005MAM00467c+0.0005MAM00468c+0.0005MAM00469c+0.0005MAM00470c+0.0005MAM00471c+0.21181-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0266MAM00474c+0.0228MAM00476c+0.0005MAM00477c+0.0005MAM00478c+0.0012MAM00479c+0.0005MAM00480c+0.0005MAM00481c+0.0005MAM00482c+0.0005MAM00483c+0.00051-dodecanoyl-sn-glycerol 3-phosphate+0.06781-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0019MAM00492c+0.00561-tetradecanoyl-sn-glycerol 3-phosphate+0.0005MAM00494c+0.136MAM00495c+0.06781-hexadecanoyl-sn-glycero-3-phosphate+0.0005MAM00497c+0.0005MAM00498c+0.35531-octadecanoyl-sn-glycero-3-phosphate+0.0005MAM00500c+0.0005MAM00501c+0.0005MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00559CC BY 4.0Reference data
0.002MAM00436c+0.002MAM00437c+0.002MAM00438c+0.002MAM00439c+0.002MAM00440c+0.002MAM00441c+0.002MAM00442c+0.002MAM00443c+0.002MAM00444c+0.002MAM00445c+0.002MAM00446c+0.002MAM00447c+0.002MAM00448c+0.002MAM00449c+0.003MAM00450c+0.002MAM00451c+0.0068MAM00452c+0.002MAM00453c+0.002MAM00454c+0.002MAM00455c+0.002MAM00456c+0.002MAM00457c+0.002MAM00458c+0.002MAM00459c+0.002MAM00460c+0.0358MAM00461c+0.002MAM00462c+0.002MAM00463c+0.002MAM00464c+0.002MAM00465c+0.002MAM00466c+0.002MAM00467c+0.002MAM00468c+0.002MAM00469c+0.002MAM00470c+0.002MAM00471c+0.01361-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0453MAM00474c+0.002MAM00476c+0.002MAM00477c+0.002MAM00478c+0.002MAM00479c+0.002MAM00480c+0.002MAM00481c+0.002MAM00482c+0.002MAM00483c+0.0021-dodecanoyl-sn-glycerol 3-phosphate+0.0251-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0075MAM00492c+0.0111-tetradecanoyl-sn-glycerol 3-phosphate+0.002MAM00494c+0.061MAM00495c+0.5571-hexadecanoyl-sn-glycero-3-phosphate+0.002MAM00497c+0.002MAM00498c+0.1381-octadecanoyl-sn-glycero-3-phosphate+0.002MAM00500c+0.002MAM00501c+0.002MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00560CC BY 4.0Reference data
0.0001MAM00436c+0.0001MAM00437c+0.0001MAM00438c+0.0001MAM00439c+0.0001MAM00440c+0.0001MAM00441c+0.0001MAM00442c+0.0001MAM00443c+0.0001MAM00444c+0.0001MAM00445c+0.0001MAM00446c+0.0001MAM00447c+0.0001MAM00448c+0.0001MAM00449c+0.0081MAM00450c+0.0016MAM00451c+0.0003MAM00452c+0.0001MAM00453c+0.0001MAM00454c+0.0001MAM00455c+0.0001MAM00456c+0.0025MAM00457c+0.0001MAM00458c+0.0018MAM00459c+0.0032MAM00460c+0.0229MAM00461c+0.0001MAM00462c+0.0001MAM00463c+0.0001MAM00464c+0.0001MAM00465c+0.0001MAM00466c+0.0001MAM00467c+0.0001MAM00468c+0.0001MAM00469c+0.0001MAM00470c+0.0001MAM00471c+0.05211-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.0217MAM00474c+0.0023MAM00476c+0.0001MAM00477c+0.0001MAM00478c+0.003MAM00479c+0.0001MAM00480c+0.0001MAM00481c+0.0001MAM00482c+0.0001MAM00483c+0.00011-dodecanoyl-sn-glycerol 3-phosphate+0.2811-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0119MAM00492c+0.00241-tetradecanoyl-sn-glycerol 3-phosphate+0.0001MAM00494c+0.4226MAM00495c+0.121-hexadecanoyl-sn-glycero-3-phosphate+0.0001MAM00497c+0.0001MAM00498c+0.03841-octadecanoyl-sn-glycero-3-phosphate+0.0001MAM00500c+0.0001MAM00501c+0.0001MAM00502c1-acyl-sn-glycerol 3-phosphate
Reaction pageLeft to rightBalance undeterminablecytosol
Human-GEM MAR00561CC BY 4.0Reference data
1-acyl-sn-glycerol 3-phosphate0.0004MAM00436c+0.0004MAM00437c+0.0004MAM00438c+0.0004MAM00439c+0.0004MAM00440c+0.0004MAM00441c+0.0004MAM00442c+0.0004MAM00443c+0.0004MAM00444c+0.0004MAM00445c+0.0004MAM00446c+0.0004MAM00447c+0.0004MAM00448c+0.0004MAM00449c+0.0278MAM00450c+0.0038MAM00451c+0.0116MAM00452c+0.0004MAM00453c+0.0004MAM00454c+0.0004MAM00455c+0.0004MAM00456c+0.0025MAM00457c+0.0004MAM00458c+0.0059MAM00459c+0.0014MAM00460c+0.0004MAM00461c+0.0004MAM00462c+0.0004MAM00463c+0.0115MAM00464c+0.0004MAM00465c+0.0004MAM00466c+0.0004MAM00467c+0.0004MAM00468c+0.0004MAM00469c+0.0004MAM00470c+0.0004MAM00471c+0.10831-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+0.025MAM00474c+0.0215MAM00476c+0.0004MAM00477c+0.0004MAM00478c+0.0029MAM00479c+0.0004MAM00480c+0.0004MAM00481c+0.0004MAM00482c+0.0004MAM00483c+0.00041-dodecanoyl-sn-glycerol 3-phosphate+0.19151-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+0.0084MAM00492c+0.01331-tetradecanoyl-sn-glycerol 3-phosphate+0.0004MAM00494c+0.1545MAM00495c+0.2221-hexadecanoyl-sn-glycero-3-phosphate+0.0219MAM00497c+0.0004MAM00498c+0.14981-octadecanoyl-sn-glycero-3-phosphate+0.0004MAM00500c+0.0004MAM00501c+0.0004MAM00502c
Reaction pageReversibleBalance undeterminablecytosol
Human-GEM MAR10035CC BY 4.0Reference data
1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+(9Z)-octadecenoyl-CoA1-(9Z,12Z)-octadecadienoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by LCLAT1
Reaction pageLeft to rightBalanced
Rhea RHEA:37135CC BY 4.0Reference data
(9Z,12Z)-octadecadienoyl-CoA+sn-glycerol 3-phosphate1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+coenzyme A(4-)
Catalysed by GPAT3 or GPAT4 or GPAM
Reaction pageLeft to rightBalanced
Rhea RHEA:37203CC BY 4.0Reference data
1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine+water1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate+choline+hydron
Catalysed by ENPP2
Reaction pageLeft to rightBalanced
Rhea RHEA:41135CC BY 4.0Reference data
Other names
12 names
Resolves to: 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate
- Also called
- 1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphate1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate(2-)1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate(2−)1-linoleoyl-GPA1-linoleoyl-GPA (18:2)GPA(18:2)LPA(18:2)LPA(18:2/0:0)PA(18:2(9Z,12Z)/0:0)PA(18:2)PA(18:2/0:0)
- Systematic name
- (2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphate