PA(16:0/18:0) (YMDB13536)

Identification
YMDB IDYMDB13536
NamePA(16:0/18:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPA(16:0/18:0) 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(16:0/18:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. 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
  • (2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl stearate
  • 1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphate
  • 1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoglycerol
  • GPG(16:0/18:0)
  • GPG(34:0)
  • PG(16:0/18:0)
  • PG(34:0)
  • Phosphatidylglycerol(16:0/18:0)
  • Phosphatidylglycerol(34:0)
  • (2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl stearic acid
  • 1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoric acid
  • PA(16:0/18:0)
  • 1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoric acid
CAS numberNot Available
WeightAverage: 676.957
Monoisotopic: 676.504306309
InChI KeyGASPGIDKILJBMM-PGUFJCEWSA-N
InChIInChI=1S/C37H73O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h35H,3-34H2,1-2H3,(H2,40,41,42)/t35-/m1/s1
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxyphosphonic acid
Chemical FormulaC37H73O8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC
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 Solubility9.1e-05 g/LALOGPS
logP9.04ALOGPS
logP12.77ChemAxon
logS-6.9ALOGPS
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
Refractivity187.77 m³·mol⁻¹ChemAxon
Polarizability84.87 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
Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/20:1(11Z))PW012594 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/20:1(13Z))PW012595 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))PW012596 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))PW012597 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/20:0)PW012598 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
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 (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0150-0000900000-ebf44982a0f744d24561JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID73254
HMDB IDNot Available
Pubchem Compound ID52929498
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available