Record Information
Version2.0
Creation Date2012-05-31 10:27:48 -0600
Update Date2015-12-09 12:10:32 -0700
Secondary Accession Numbers
  • ECMDB00614
Identification
Name:PS(16:0/16:0)
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:
  • 1,2-dihexadecanoyl-rac-glycero-3-phosphoserine
  • 1,2-dipalmitoyl-rac-glycero-3-phosphoserine
  • 1,2-Dipalmitoylglycerophosphorylserine
  • 1,2-Dipalmitoylphosphatidylserine
  • Dipalmitoyl-DL-a-phosphatidyl-L-serine
  • Dipalmitoyl-DL-alpha-phosphatidyl-L-serine
  • Dipalmitoyl-DL-α-phosphatidyl-L-serine
  • Dipalmitoylglycerophosphoserine
  • Dipalmitoylphosphatidylserine
  • DL-a-Dipalmitoyl phosphatidyl-L-serine
  • DL-alpha-Dipalmitoyl phosphatidyl-L-serine
  • DL-α-Dipalmitoyl phosphatidyl-L-serine
  • DPPS
  • Phosphatidylserine (16:0/16:0)
  • Phosphatidylserine (32:0)
  • Phosphatidylserine(16:0/16:0)
  • Phosphatidylserine(32:0)
  • PS(32:0)
  • PSer(16:0/16:0)
  • PSer(32:0)
Chemical Formula:C38H74NO10P
Weight:Average: 735.9686
Monoisotopic: 735.505034105
InChI Key:KLFKZIQAIPDJCW-GPOMZPHUSA-N
InChI:InChI=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
CAS number:3036-82-6
IUPAC Name:(2S)-2-amino-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name:dipalmitoyl phosphatidylserine
SMILES:CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC
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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00011 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 Locations:Membrane
Reactions:
CDP-1,2-didodecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-dihexadec-9-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-dihexadecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-dioctadec-11-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-Dioctadecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-ditetradec-7-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-ditetradecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0)
Hydrogen ion + PS(16:0/16:0) > Carbon dioxide + PE(14:0/14:0)
CDP-diacylglycerol + L-Serine <> Cytidine monophosphate + PS(16:0/16:0)
PS(16:0/16:0) <> PE(14:0/14:0) + Carbon dioxide
PS(16:0/16:0) + Water <> 2-Acyl-sn-glycero-3-phosphoserine + Fatty acid
CDP-DG(16:0/16:0) + L-Serine + CDP-DG(16:0/16:0) + L-Serine > Hydrogen ion + Cytidine monophosphate + PS(16:0/16:0) + Cytidine monophosphate
PS(16:0/16:0) + Hydrogen ion > PE(16:0/16:0) + Carbon dioxide
PS(16:0/16:0) + Hydrogen ion > PE(16:0/15:0) + Carbon dioxide
PS(16:0/16:0) + Hydrogen ion > PE(15:0/16:0) + Carbon dioxide
CDP-diacylglycerol + L-Serine <> Cytidine monophosphate + PS(16:0/16:0)
Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0)
Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0)
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/16:0/17:0cycw7c/16:0))PW001584 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/16:1(9Z))PW001063 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:0)PW001072 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/16:1(9Z))PW001096 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:0/16:0/16:0)PW001100 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/15:0cyclo)PW001107 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/16:1(9Z))PW001108 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:0/18:1(9Z)/18:1(9Z))PW001113 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:0/16:1(9Z))PW001125 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:0)PW001128 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:1(9Z))PW001129 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/18:1(9Z))PW001138 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/16:0/18:1(9Z))PW001166 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/16:0)PW001174 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/16:1(9Z))PW001222 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/16:0/16:0)PW001226 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/16:1(9Z)/15:0cyclo)PW001231 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/16:1(9Z)/16:1(9Z))PW001235 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/18:1(9Z)/18:1(9Z))PW001243 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:0/16:1(9Z))PW001449 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/16:0)PW001452 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0000393000-5d82d8d3c3cc3a8e1ef7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0000016900-6bb9b6bacde6d8b4611bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000002900-eaf2a2217a8f79f1c16cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090033100-708416ca737a3b1fee06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000010900-db7bc8c2e3b9dad9960cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0001391600-51c373de4449f596bd5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001391100-9a4a9ad709f158064e08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-14i6-0000099900-38c346454df0c2d55b3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0900099900-cf1ed9c46228bdf4f23fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-0900099900-cf1ed9c46228bdf4f23fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-402c44be8653ebc0c284View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000001900-2b5ae18fbcabd46b8f69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-0166109600-e8d10538897e7b62801eView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Chen S: Partial characterization of the molecular species of phosphatidylserine from human plasma by high-performance liquid chromatography and fast atom bombardment mass spectrometry. J Chromatogr B Biomed Appl. 1994 Nov 4;661(1):1-5. Pubmed: 7866537
  • Gao F, Tian X, Wen D, Liao J, Wang T, Liu H: Analysis of phospholipid species in rat peritoneal surface layer by liquid chromatography/electrospray ionization ion-trap mass spectrometry. Biochim Biophys Acta. 2006 Jul;1761(7):667-76. Epub 2006 Apr 24. Pubmed: 16714143
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. Pubmed: 890917
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Hermetter, A.; Paltauf, F.; Hauser, H. Synthesis of diacyl and alkylacyl glycerophosphoserines. Chemistry and Physics of Lipids (1982), 30(1), 35-45.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID84523
HMDB IDHMDB00614
Pubchem Compound ID3081382
Kegg IDC02737
ChemSpider ID2338998
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Uniprot ID:
P0A8K1
Molecular weight:
35934
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.
General function:
Not Available
Specific function:
Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:
crcA
Uniprot ID:
P37001
Molecular weight:
21770
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine
Gene Name:
pssA
Uniprot ID:
P23830
Molecular weight:
52801
Reactions
CDP-diacylglycerol + L-serine = CMP + (3-sn-phosphatidyl)-L-serine.

Transporters

General function:
Involved in phospholipid transporter activity
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaB
Uniprot ID:
P64602
Molecular weight:
10680
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaD
Uniprot ID:
P64604
Molecular weight:
19576
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Uniprot ID:
P64606
Molecular weight:
27863