Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120513
Name: 1-18:1-2-18:1-phosphatidate
Description:PA(18:1(9Z)/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:1(9Z)/18:1(9Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of oleic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218 , 16185776 ).
  • 18:1-18:1-PA
  • 1-18:1-2-18:1-phosphatidic acid
  • 1,2-(9Z-octadecenoyl)-sn-glycero-3-phosphate
Chemical Formula: C39H71O8P
Average Molecular Weight: 698.959
Monoisotopic Molecular Weight: 700.50433
CAS number: 14268-17-8
IUPAC Name:[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name: (2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassGlycerophospholipids
Direct Parent 1,2-diacylglycerol-3-phosphates
Alternative Parents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:Not Available
Melting point: Not Available
Experimental Properties:
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility6.69e-05 mg/mLALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity199.21 m3·mol-1ChemAxon
Polarizability85.16 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
  • superpathway phosphatidate biosynthesis (yeast)PWY-7411
    Spectrum TypeDescriptionSplash Key
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1161905400-772a04939f580ad71d3aView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2393525000-2715e13ba0037dd569f5View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y0-0196143000-d804e12c01cbda475d7fView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01sj-4090403000-66c0da756ade4dd045cdView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050100000-bada02a9f3dfb4726aecView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-60c4b63129e42338dbf2View in MoNA
    • Niedernberg A, Tunaru S, Blaukat A, Ardati A, Kostenis E: Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63. Cell Signal. 2003 Apr;15(4):435-46. [12618218 ]
    • Park KA, Vasko MR: Lipid mediators of sensitivity in sensory neurons. Trends Pharmacol Sci. 2005 Nov;26(11):571-7. Epub 2005 Sep 26. [16185776 ]
    Synthesis Reference: Hermetter, A.; Paltauf, F.; Hauser, H. Synthesis of diacyl and alkylacyl glycerophosphoserines. Chemistry and Physics of Lipids (1982), 30(1), 35-45.
    Material Safety Data Sheet (MSDS) Not Available
    External Links: