PS(16:0/16:0) (PAMDB000157)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000157
Identification
Name: PS(16:0/16:0)
Description:PS(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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 735.9686
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoserines
Direct Parent Phosphatidylserines
Alternative Parents
Substituents
  • Diacyl-glycerol-3-phosphoserine
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000105 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count40ChemAxon
Refractivity196.83 m3·mol-1ChemAxon
Polarizability88.45 Å3ChemAxon
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)
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
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

Protein Details
• Phosphatidylserine decarboxylase proenzyme
General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Locus Tag:
PA4957
Molecular weight:
32 kDa
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
Protein Details
• CDP-diacylglycerol--serine O-phosphatidyltransferase
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
Locus Tag:
PA4693
Molecular weight:
29.3 kDa
Reactions
CDP-diacylglycerol + L-serine = CMP + (3-sn-phosphatidyl)-L-serine.

Transporters

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
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
Locus Tag:
PA4455
Molecular weight:
28.4 kDa