PA(18:1(9Z)/18:1(9Z)) (YMDB01169)

Identification
YMDB IDYMDB01169
NamePA(18:1(9Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPA(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 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
MOLSDFPDBSMILESInChI
Synonyms
  • 1,2-di(9Z-octadecenoyl)-rac-phosphatidic acid
  • 1,2-Diacyl-sn-glycerol 3-phosphate
  • 1,2-dioleoyl-rac-glycero-3-phosphate
  • 1,2-Dioleoyl-sn-glycero-3-phosphate
  • 1,2-dioleoylglycerol-3-phosphate
  • 3-sn-Phosphatidate
  • Dioleoylphosphatidic acid
  • DOPA
  • PA(18:1(9Z)/18:1(9Z))[U]
  • PA(18:1/18:1)
  • PA(18:1/18:1)[U]
  • PA(18:1n9/18:1n9)
  • PA(18:1w9/18:1w9)
  • PA(36:2)
  • Phosphatidate
  • Phosphatidic acid
  • Phosphatidic acid(18:1/18:1)
  • Phosphatidic acid(18:1n9/18:1n9)
  • Phosphatidic acid(18:1w9/18:1w9)
  • Phosphatidic acid(36:2)
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphate
  • 1-18:1-2-18:1-Phosphatidic acid
  • PA(18:1OMEGA9/18:1OMEGA9)
  • Phosphatidic acid(18:1omega9/18:1omega9)
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphoric acid
  • 1-18:1-2-18:1-Phosphatidate
  • Phosphatidate(18:1/18:1)
  • Phosphatidate(18:1N9/18:1N9)
  • Phosphatidate(18:1OMEGA9/18:1OMEGA9)
  • Phosphatidate(36:2)
CAS number14268-17-8
WeightAverage: 700.979
Monoisotopic: 700.504306309
InChI KeyMHUWZNTUIIFHAS-DSSVUWSHSA-N
InChIInChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37H,3-16,21-36H2,1-2H3,(H2,42,43,44)/b19-17-,20-18-/t37-/m1/s1
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 FormulaC39H73O8P
SMILES[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC
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
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.7e-05 g/LALOGPS
logP9.13ALOGPS
logP12.93ChemAxon
logS-7ALOGPS
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 Count38ChemAxon
Refractivity199.21 m³·mol⁻¹ChemAxon
Polarizability85.27 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))PW007898 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerol metabolismPW002407 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Glycerophospholipid metabolismec00564 Map00564
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1161905400-772a04939f580ad71d3aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2393525000-2715e13ba0037dd569f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y0-0196143000-d804e12c01cbda475d7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01sj-4090403000-66c0da756ade4dd045cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050100000-bada02a9f3dfb4726aecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-60c4b63129e42338dbf2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000009000-55a7c1167cbe0f25b0beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00l2-1160709000-29509e1741f42c75d166JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1190301000-37df9990afdea06a6940JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0000009500-c84c90ec7d2e858c69f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000007900-6386210cf4e9425daf33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0000509100-163cface94c4f3099804JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-af2da6ae565960d02a74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00i0-0000009900-7e41e59856bf50ddbb3cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i3-0000904600-65f32117a29942491df4JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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
Synthesis Reference:Hermetter, A.; Paltauf, F.; Hauser, H. Synthesis of diacyl and alkylacyl glycerophosphoserines. Chemistry and Physics of Lipids (1982), 30(1), 35-45.
External Links:
ResourceLink
CHEBI ID60427
HMDB IDHMDB07865
Pubchem Compound ID5873088
Kegg IDC00416
ChemSpider ID21403062
FOODB IDNot Available
WikipediaLecithin
BioCyc IDCPD-8268