PA(14:0/18:1(9Z)) (YMDB13488)

Identification
YMDB IDYMDB13488
NamePA(14:0/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPA(14:0/18:1(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(14:0/18:1(9Z)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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
  • 1-Tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate
  • 1-Tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate
  • PA(14:0/18:1)
  • 1-Tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoric acid
  • 1-Tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoric acid
CAS numberNot Available
WeightAverage: 646.887
Monoisotopic: 646.457356115
InChI KeyIZDWXHIHOWRUTO-NTEJXHNLSA-N
InChIInChI=1S/C35H67O8P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(37)43-33(32-42-44(38,39)40)31-41-34(36)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,33H,3-15,18-32H2,1-2H3,(H2,38,39,40)/b17-16-/t33-/m1/s1
IUPAC Name[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxyphosphonic acid
Chemical FormulaC35H67O8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCC)(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 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
Polarizability79.12 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(14:0/18:1(9Z)/14:0/18:1(11Z))PW009288 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/18:1(9Z)/14:0/18:1(9Z))PW009289 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/18:1(9Z)/18:1(11Z)/18:1(11Z))PW009290 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/18:1(9Z)/18:1(11Z)/18:1(9Z))PW009291 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/18:1(9Z)/18:1(11Z)/20:0)PW009292 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, Positivesplash10-03di-0000900000-bbd1b53228dca48397d5JSpectraViewer
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 ID74943
HMDB IDNot Available
Pubchem Compound ID9547164
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available