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Record Information
StatusExpected but not Quantified
Creation Date2017-09-09 03:20:18 UTC
Update Date2019-07-23 09:19:08 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NamePA(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
DescriptionPA(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) 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(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of alpha-linolenic acid at the C-1 position and one chain of alpha-linolenic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
1-alpha-linolenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB
1-alpha-linolenoyl-2-alpha-linolenoyl-sn-phosphatidic acid SMPDB, HMDB
PA(18:3/18:3) SMPDB, HMDB
PA(18:3n3/18:3n3) SMPDB, HMDB
PA(18:3w3/18:3w3) SMPDB, HMDB
Phosphatidic acid(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB
Phosphatidic acid(18:3/18:3) SMPDB, HMDB
Phosphatidic acid(18:3n3/18:3n3) SMPDB, HMDB
Phosphatidic acid(18:3w3/18:3w3) SMPDB, HMDB
Phosphatidic acid(36:6) SMPDB, HMDB
Phosphatidate(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB
Phosphatidate(18:3/18:3) SMPDB, HMDB
Phosphatidate(18:3n3/18:3n3) SMPDB, HMDB
Phosphatidate(18:3w3/18:3w3) SMPDB, HMDB
Phosphatidate(36:6)SMPDB, HMDB
Chemical FormulaC39H65O8P
Average Molecular Weight692.915
Monoisotopic Molecular Weight692.441706051
IUPAC Name[(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycerophosphates
Direct Parent1,2-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physiological effect

Organoleptic effect:


Route of exposure:


Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity203.68 m³·mol⁻¹ChemAxon
Polarizability81.71 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tc-1152927000-c80aaf25bdcdd4ca4d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ta-3296663000-d39ad2f64d77d0caff04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1169262000-f1aecc6e93cb0a5ffbfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-4090303000-dac866d376813a7e0871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-9b9f3e8e1bdff86a6bd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-27a50455f00a367691f9Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot 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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547161
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
  2. Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
  3. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
  9. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.