General Information of MET (ID: META00002)
Name LysoPA(18:1(9Z)/0:0)
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-(9Z-Octadecenoyl)-glycero-3-phosphate; 1-(9Z-Octadecenoyl)-phosphatidic acid; 1-O-Oleyllysophosphatidic acid; 1-Oleoyl-glycero-3-phosphate; 1-Oleoyl-lyso-phosphatidic acid; 1-Oleoyl-lysophosphatidic acid; 9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester; LPA (lysophosphatidic acid); LPA(18:1(9Z)/0:0); LPA(18:1); LPA(18:1/0:0); Lysophosphatidic acid; Lysophosphatidic acid(18:1); Lysophosphatidic acid(18:1/0:0); MOPA; Monooleylphosphatidate; Monooleylphosphatidic acid; Monooleylphosphatidic acid, (R)-isomer; Monooleylphosphatidic acid, sodium salt, (R)-isomer
Source Aliphatic acyclic compounds
Structure Type   Glycerophosphates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Glycerophospholipids
Glycerophosphates
PubChem CID
5497152
HMDB ID
HMDB0007855
Formula
C21H41O7P
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
Physicochemical Properties Molecular Weight 436.5 Topological Polar Surface Area 113
XlogP 5.2 Complexity 462
Heavy Atom Count 29 Rotatable Bond Count 21
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Function
LysoPA(18:1(9Z)/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers. LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils. In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Lysophosphatidate-3 receptor (LPAR3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation LysoPA(18:1(9Z)/0:0) addition (1 hours)
                      Induced Change LPAR3 protein expression levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Motor neuron disease [ICD-11: 8B60]
                      Details It is reported that lysoPA(18:1(9Z)/0:0) addition causes the increase of LPAR3 protein expression compared with control group.
      Transferases (EC 2)
            Signal-regulated kinase 1 (ERK1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation LysoPA(18:1(9Z)/0:0) addition (0.08 hours)
                      Induced Change MAPK3 protein phosphorylation levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Idiopathic pulmonary fibrosis [ICD-11: CB03] ...
                      Details It is reported that lysoPA(18:1(9Z)/0:0) addition causes the increase of MAPK3 protein phosphorylation compared with control group.
            Signal-regulated kinase 2 (ERK2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation LysoPA(18:1(9Z)/0:0) addition (0.08 hours)
                      Induced Change MAPK1 protein phosphorylation levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Idiopathic pulmonary fibrosis [ICD-11: CB03] ...
                      Details It is reported that lysoPA(18:1(9Z)/0:0) addition causes the increase of MAPK1 protein phosphorylation compared with control group.
References
1 Molecular cloning and characterization of a novel human G-protein-coupled receptor, EDG7, for lysophosphatidic acid. J Biol Chem. 1999 Sep 24;274(39):27776-85.
2 Antidepressants induce profibrotic responses via the lysophosphatidic acid receptor LPA 1. Eur J Pharmacol. 2020 Apr 15;873:172963.

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