PA(12:0/20:1(13Z)) (YMDB13486)

Identification
YMDB IDYMDB13486
NamePA(12:0/20:1(13Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPA(12:0/20:1(13Z)) 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(12:0/20:1(13Z)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 13Z-eicosenoyl 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 646.887
Monoisotopic: 646.457356115
InChI KeyLTSFUQJGUQGAMK-BLACGIAASA-N
InChIInChI=1S/C35H67O8P/c1-3-5-7-9-11-13-14-15-16-17-18-19-20-22-24-26-28-30-35(37)43-33(32-42-44(38,39)40)31-41-34(36)29-27-25-23-21-12-10-8-6-4-2/h13-14,33H,3-12,15-32H2,1-2H3,(H2,38,39,40)/b14-13-/t33-/m1/s1
IUPAC Name[(2R)-3-(dodecanoyloxy)-2-[(13Z)-icos-13-enoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name(2R)-3-(dodecanoyloxy)-2-[(13Z)-icos-13-enoyloxy]propoxyphosphonic acid
Chemical FormulaC35H67O8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCC
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
  • Monoalkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.9e-05 g/LALOGPS
logP8.55ALOGPS
logP11.52ChemAxon
logS-6.8ALOGPS
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 Count35ChemAxon
Refractivity179.69 m³·mol⁻¹ChemAxon
Polarizability79.23 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(12:0/20:1(13Z)/12:0/20:1(11Z))PW008049 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:1(13Z)/12:0/20:1(13Z))PW008050 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:1(13Z)/20:1(11Z)/20:1(11Z))PW008051 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:1(13Z)/20:1(11Z)/20:1(13Z))PW008052 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:1(13Z)/20:1(13Z)/20:1(11Z))PW008053 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_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001o-0009900000-03a6f75154d2db82ec3dJSpectraViewer
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 IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available