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Record Information
StatusExpected but not Quantified
Creation Date2008-09-12 01:27:14 UTC
Update Date2017-12-23 08:00:10 UTC
Secondary Accession Numbers
  • HMDB00443
  • HMDB07855
Metabolite Identification
Common NameLysoPA(18:1(9Z)/0:0)
DescriptionLysoPA(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 (PMID 11585410 ). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233 ). 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. (PMID 15271293 ).
1-O-Oleyllysophosphatidic acidMeSH
1-Oleoyl-lysophosphatidic acidMeSH
LPA (lysophosphatidic acid)MeSH
Monooleylphosphatidic acidMeSH
Monooleylphosphatidic acid, (R)-isomerMeSH
Monooleylphosphatidic acid, sodium salt, (R)-isomerMeSH
1-(9Z-octadecenoyl)-glycero-3-phosphate; 1-oleoyl-glycero-3-phosphateLipid Annotator
Lysophosphatidic Acid(18:1)Lipid Annotator
Lysophosphatidic Acid(18:1/0:0)Lipid Annotator
LPA(18:1/0:0)Lipid Annotator
LPA(18:1)Lipid Annotator
LPA(18:1(9Z)/0:0)Lipid Annotator
1-(9Z-octadecenoyl)-phosphatidic acidLipid Annotator
1-(9Z-octadecenoyl)-glycero-3-phosphateLipid Annotator
1-oleoyl-glycero-3-phosphateLipid Annotator
Chemical FormulaC21H41O7P
Average Molecular Weight436.526
Monoisotopic Molecular Weight436.258990658
IUPAC Name{2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy}phosphonic acid
Traditional Namelysophosphatidic acid
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycerophosphates
Direct Parent1-acylglycerol-3-phosphates
Alternative Parents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0016 g/LALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity115.3 m³·mol⁻¹ChemAxon
Polarizability49.95 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01c0-5950100000-b87ae65c3f28df11b01bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:0)Pw029768Pw029768 greyscalePw029768 simpleNot Available
Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:1(9Z))Pw029769Pw029769 greyscalePw029769 simpleNot Available
Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:0)Pw029770Pw029770 greyscalePw029770 simpleNot Available
Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(11Z))Pw029771Pw029771 greyscalePw029771 simpleNot Available
Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(9Z))Pw029772Pw029772 greyscalePw029772 simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLysophosphatidic acid
METLIN IDNot Available
PubChem Compound5497152
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shen Z, Wu M, Elson P, Kennedy AW, Belinson J, Casey G, Xu Y: Fatty acid composition of lysophosphatidic acid and lysophosphatidylinositol in plasma from patients with ovarian cancer and other gynecological diseases. Gynecol Oncol. 2001 Oct;83(1):25-30. [PubMed:11585410 ]
  2. Gerrard JM, Clawson CC, White JG: Lysophosphatidic acids: III. Enhancement of neutrophil chemotaxis. Am J Pathol. 1980 Sep;100(3):609-18. [PubMed:7416233 ]
  3. Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89. [PubMed:15271293 ]

Only showing the first 10 proteins. There are 46 proteins in total.


General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:
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General function:
Involved in diacylglycerol kinase activity
Specific function:
Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:
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General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
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Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:
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Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
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Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:
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General function:
Involved in diacylglycerol kinase activity
Specific function:
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
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Only showing the first 10 proteins. There are 46 proteins in total.