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Identification
YMDB IDYMDB01170
NamePA(18:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPA(18:1(9Z)/0:0)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)/0:0), in particular, consists of two 9Z-octadecenoyl chain at positions C-1 and C2. 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.
Structure
Thumb
Synonyms
  • 1-Acyl-sn-glycerol 3-phosphate
  • 2-Lysophosphatidate
  • LPA
  • Lysophosphatidate
  • 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphate
  • 1-O-Oleoyl-sn-glycerol 3-phosphate
  • 1-O-Oleyl-sn-glycerol 3-phosphate
  • 1-Oleoyl lysophosphatidic acid
  • 1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidic acid
  • 1-Oleoyl-sn-glycero-3-phosphate
  • 1-Oleoylglycerol 3-phosphate
  • 1-Oleyl-2-lyso-sn-glycerol 3-phosphatidic acid
  • 1-Oleyl-sn-glycerol 3-phosphate
  • 1-Oleylglycerol 3-phosphate
  • 1-Oleyllysophosphatidic acid
  • 18:1 LPA
  • LPA 18:1
  • LPA(18:1(9Z)/0:0)
  • LPA(18:1)
  • LPA(18:1/0:0)
  • LPA(18:1n9/0:0)
  • LPA(18:1W9/0:0)
  • LysoPA(18:1(9Z)/0:0)
  • LysoPA(18:1)
  • LysoPA(18:1W9/0:0)
  • Lysophosphatidic acid(18:1)
  • Lysophosphatidic acid(18:1/0:0)
  • Lysophosphatidic acid(18:1n9/0:0)
  • Lysophosphatidic acid(18:1W9/0:0)
  • Monooleylphosphatidic acid
  • PA(18:1/0:0)
  • 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphoric acid
  • 1-O-Oleoyl-sn-glycerol 3-phosphoric acid
  • 1-O-Oleyl-sn-glycerol 3-phosphoric acid
  • 1-Oleoyl lysophosphatidate
  • 1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidate
  • 1-Oleoyl-sn-glycero-3-phosphoric acid
  • 1-Oleoylglycerol 3-phosphoric acid
  • 1-Oleyl-2-lyso-sn-glycerol 3-phosphatidate
  • 1-Oleyl-sn-glycerol 3-phosphoric acid
  • 1-Oleylglycerol 3-phosphoric acid
  • 1-Oleyllysophosphatidate
  • Lysophosphatidate(18:1)
  • Lysophosphatidate(18:1/0:0)
  • Lysophosphatidate(18:1n9/0:0)
  • Lysophosphatidate(18:1W9/0:0)
  • Monooleylphosphatidate
  • 1-O-Oleyllysophosphatidic acid
  • 9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester
  • 1-Oleoyl-lyso-phosphatidic acid
  • Monooleylphosphatidic acid, sodium salt, (R)-isomer
  • 1-Oleoyl-lysophosphatidic acid
  • LPA (lysophosphatidic acid)
  • Lysophosphatidic acid
  • Monooleylphosphatidic acid, (R)-isomer
  • MOPA
CAS number22002-87-5
WeightAverage: 436.5198
Monoisotopic: 436.258990178
InChI KeyWRGQSWVCFNIUNZ-GDCKJWNLSA-N
InChIInChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1
IUPAC Name[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name1-oleoyl lysophosphatidic acid
Chemical FormulaC21H41O7P
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O
Chemical Taxonomy
Description 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
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 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 Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP4.69ALOGPS
logP5.49ChemAxon
logS-5.4ALOGPS
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
Polarizability49.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondrion membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Glycerophospholipid metabolismec00564 Map00564
SMPDB ReactionsNot Available
KEGG Reactions
acyl-CoA + PA(18:1(9Z)/0:0)hydron + LPA(16:0/0:0) + Coenzyme A
acyl-CoA + Glycerol 3-phosphatePA(18:1(9Z)/0:0) + Coenzyme A + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-1664900000-148c650ac3bceb4b152cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-3962100000-1a33e6ed4c6ff2881be4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avr-7790000000-f51fa6e6693ad7c3d713JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01s9-4190400000-e613f5b69c617ba039f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-939e9b478cb01e4cdf3bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5a4a918141c40ba8ca5dJSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Oshiro, J., Han, G. S., Carman, G. M. (2003). "Diacylglycerol pyrophosphate phosphatase in Saccharomyces cerevisiae." Biochim Biophys Acta 1635:1-9.14642771
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID52288
HMDB IDNot Available
Pubchem Compound ID5311263
Kegg IDC00681
ChemSpider ID4470776
FOODB IDNot Available
WikipediaLysophosphatidic_acid
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the dephosphorylation of diacylglycerol phosphate (DGPP) to phosphatidate (PA) and the subsequent dephosphorylation of PA to diacylglycerol (DAG). Together with DPP1, regulates intracellular DGPP and PA levels which are phospholipid molecules believed to play a signaling role in stress response. Can also use lysophosphatidic acid (LPA) as a substrate. Substrate preference is PA > DGPP > LPA
Gene Name:
LPP1
Uniprot ID:
Q04396
Molecular weight:
31585.90039
Reactions
A 1,2-diacylglycerol 3-phosphate + H(2)O → a 1,2-diacyl-sn-glycerol + phosphate.
Diacylglycerol pyrophosphate + H(2)O → phosphatidate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the dephosphorylation of diacylglycerol phosphate (DGPP) to phosphatidate (PA) and the subsequent dephosphorylation of PA to diacylglycerol (DAG). Together with LPP1, regulates intracellular DGPP and PA levels which are phospholipid molecules believed to play a signaling role in stress response. Can also use lysophosphatidic acid (LPA) as a substrate. Substrate preference is DGPP > LPA > PA
Gene Name:
DPP1
Uniprot ID:
Q05521
Molecular weight:
33513.60156
Reactions
A 1,2-diacylglycerol 3-phosphate + H(2)O → a 1,2-diacyl-sn-glycerol + phosphate.
Diacylglycerol pyrophosphate + H(2)O → phosphatidate + phosphate.