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Identification
YMDB IDYMDB01251
NamePS(16:0/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPS(16:0/16:0) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PS(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
Structure
Thumb
Synonyms
  • 1-D-phosphatidyl-L-serine
  • 1,2-Diacyl-sn-glycerol 3-phospho-L-serine
  • 1,2-dipalmitoyl-rac-glycero-3-phosphoserine
  • 1,2-Dipalmitoylglycerophosphorylserine
  • 1,2-Dipalmitoylphosphatidylserine
  • 3-L-phosphatidyl-L-serine
  • 3-O-sn-Phosphatidyl-L-serine
  • 3-sn-phosphatidyl-L-serines
  • Dipalmitoyl-DL-a-phosphatidyl-L-serine
  • Dipalmitoyl-DL-alpha-phosphatidyl-L-serine
  • Dipalmitoylglycerophosphoserine
  • Dipalmitoylphosphatidylserine
  • DL-a-Dipalmitoyl phosphatidyl-L-serine
  • DL-alpha-Dipalmitoyl phosphatidyl-L-serine
  • DPPS
  • L-alpha-phosphatidylserine
  • O3-Phosphatidyl-L-serine
  • Phosphatidyl-L-serine
  • Phosphatidylserine
  • Phosphatidylserine (16:0/16:0)
  • Phosphatidylserine (32:0)
  • Phosphatidylserine(16:0/16:0)
  • Phosphatidylserine(32:0)
  • PS(16:0/16:0)
  • PS(32:0)
  • PSer(16:0/16:0)
  • PSer(32:0)
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphoserine
  • 1,2-Dihexadecanoyl-rac-glycero-3-phosphoserine
  • 1,2-Dipalmitoyl-GPS
  • 1,2-Dipalmitoyl-sn-3-glycerophosphoserine
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphatidylserine
  • 1,2-Dipalmitoyl-sn-glycero-3-phospho-L-serine
  • Dipalmitoyl-sn-glycerol-3-phosphorylserine
  • L-alpha-Dipalmitoylphosphatidylserine
  • L-α-Dipalmitoylphosphatidylserine
CAS number3036-82-6
WeightAverage: 735.981
Monoisotopic: 735.505034585
InChI KeyKLFKZIQAIPDJCW-GPOMZPHUSA-N
InChIInChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34-,35+/m1/s1
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Namedipalmitoyl phosphatidylserine
Chemical FormulaC38H74NO10P
SMILES[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoserines
Direct ParentPhosphatidylserines
Alternative Parents
Substituents
  • Diacyl-glycerol-3-phosphoserine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • 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 Solubility0.0001 g/LALOGPS
logP4.32ALOGPS
logP9.49ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.68 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity196.83 m³·mol⁻¹ChemAxon
Polarizability88.45 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
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(16:0/16:0)PW002784 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:0/16:0)PW002753 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycine, serine and threonine metabolismec00260 Map00260
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
3000 ± 700 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
13750 ± 1675 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0000393000-5d82d8d3c3cc3a8e1ef7JSpectraViewer
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:
  • 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 ID11750
HMDB IDHMDB00614
Pubchem Compound ID3081382
Kegg IDC02737
ChemSpider ID7826040
FOODB IDFDB022144
Wikipedia IDNot Available
BioCyc IDNot Available