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Record Information
Version	2.0
Creation Date	2015-09-08 17:49:40 -0600
Update Date	2015-12-09 17:02:40 -0700
Secondary Accession Numbers	ECMDB24144
Identification
Name:	PS(16:0/18:0)
Description	PS(16:0/18:0) 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 atoms.. PS(16:0/18:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa931a2a0> Close
Synonyms:	Not Available
Chemical Formula:	C40H78NO10P
Weight:	Average: 764.035 Monoisotopic: 763.536334714
InChI Key:	UYGORIHCWHGAJE-FZNHDDJXSA-N
InChI:	InChI=1S/C40H78NO10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(43)51-36(34-49-52(46,47)50-35-37(41)40(44)45)33-48-38(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h36-37H,3-35,41H2,1-2H3,(H,44,45)(H,46,47)/t36-,37-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R)-2-amino-3-({[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name:	(2R)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
SMILES:	[H][C@@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Glycerophospholipids
Sub Class	Glycerophosphoserines
Direct Parent	Phosphatidylserines
Alternative Parents	D-alpha-amino acids Tricarboxylic acids and derivatives Phosphoethanolamines Fatty acid esters Dialkyl phosphates Carboxylic acid esters Amino acids Carboxylic acids Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Diacyl-glycerol-3-phosphoserine Alpha-amino acid Alpha-amino acid or derivatives D-alpha-amino acid Tricarboxylic acid or derivatives Phosphoethanolamine Fatty acid ester Dialkyl phosphate Organic phosphoric acid derivative Phosphoric acid ester Fatty acyl Alkyl phosphate Amino acid Carboxylic acid ester Amino acid or derivatives Carboxylic acid Carboxylic acid derivative Organic nitrogen compound Organooxygen compound Organonitrogen compound Primary aliphatic amine Organic oxide Carbonyl group Hydrocarbon derivative Primary amine Organic oxygen compound Amine Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 8.3e-05 g/L ALOGPS logP 4.66 ALOGPS logP 10.38 ChemAxon logS -7 ALOGPS pKa (Strongest Acidic) 1.47 ChemAxon pKa (Strongest Basic) 9.38 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 171.68 Ų ChemAxon Rotatable Bond Count 42 ChemAxon Refractivity 206.04 m³·mol⁻¹ ChemAxon Polarizability 92.11 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	CDP-DG(19:1(9Z)/18:1(9Z)) + L-Serine + L-Serine > PS(16:0/18:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate CDP-DG(16:0/18:0) + L-Serine + CDP-DG(16:0/18:0) + L-Serine > PS(16:0/18:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PS(16:0/18:0) + Hydrogen ion > PE(16:0/18:0) + Carbon dioxide PS(16:0/18:0) + Hydrogen ion > PE(14:0/20:0) + Carbon dioxide
SMPDB Pathways:	phospholipid biosynthesis (PE(16:0/18:0)) PW001748 phospholipid biosynthesis CL(16:0/17:0cycw7c/19:0cycv8c/19:0cycv8c) PW001354 phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/19:0cycv8c) PW001378 phospholipid biosynthesis CL(16:0/18:1(9Z)/19:0cycv8c/18:1(9Z)) PW001380 phospholipid biosynthesis CL(16:0/18:1(9Z)/19:0cycv8c/19:0cycv8c) PW001381 phospholipid biosynthesis CL(16:0/19:0cycv8c/17:0cycw7c/19:0cycv8c) PW001401 phospholipid biosynthesis CL(16:0/19:0cycv8c/18:1(9Z)/18:1(9Z)) PW001402 phospholipid biosynthesis CL(16:0/19:0cycv8c/18:1(9Z)/19:0cycv8c) PW001409 phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/17:0cycw7c) PW001412 phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/18:1(9Z)) PW001413 phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/19:0cycv8c/19:0cycv8c) PW001570 phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c) PW001605 phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/18:1(9Z)) PW001611 phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/19:0cycv8c) PW001614 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/17:0cycw7c/19:0cycv8c) PW001631 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/18:1(9Z)) PW001636 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/19:0cycv8c) PW001637 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/17:0cycw7c) PW001642 phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/18:1(9Z)) PW001643
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-9040110300-a382829ec95642bda2c3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000l-9020000000-9df5c99f1ceafa8b0226 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000f-9151011000-d86595a563306538e334 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0bwi-1190101200-27388459ec523e91f534 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a7r-5290100000-6eb11381166db19311d8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9030000000-9b453b582957810c191e View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID Not Available Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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