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Record Information
Version	2.0
Creation Date	2015-09-08 19:51:20 -0600
Update Date	2015-12-09 12:11:23 -0700
Secondary Accession Numbers	ECMDB24629
Identification
Name:	PS(19:0cycw8c/10:0)
Description	PS(19:0cycw8c/10:0) 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(19:0cycw8c/10:0), in particular, consists of one 9-(2-heptylcyclopropyl)nonanoyl chain to the C-1 atom, and one decanoyl 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:0x9f9c0fb4> Close
Synonyms:	Not Available
Chemical Formula:	C35H66NO10P
Weight:	Average: 691.884 Monoisotopic: 691.442434327
InChI Key:	KAAQOMGTBSINPK-JWWJSXKFSA-N
InChI:	InChI=1S/C35H66NO10P/c1-3-5-7-9-10-16-20-24-34(38)46-31(27-44-47(41,42)45-28-32(36)35(39)40)26-43-33(37)23-19-15-12-11-14-18-22-30-25-29(30)21-17-13-8-6-4-2/h29-32H,3-28,36H2,1-2H3,(H,39,40)(H,41,42)/t29?,30?,31-,32+/m1/s1
CAS number:	Not Available
IUPAC Name:	(2S)-2-amino-3-({[(2R)-2-(decanoyloxy)-3-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name:	(2S)-2-amino-3-{[(2R)-2-(decanoyloxy)-3-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}propanoic acid
SMILES:	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC1CC1CCCCCCC)OC(=O)CCCCCCCCC)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	L-alpha-amino acids Tricarboxylic acids and derivatives Carbocyclic fatty acids 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 L-alpha-amino acid Carbocyclic fatty acid Tricarboxylic acid or derivatives Phosphoethanolamine Dialkyl phosphate Fatty acid ester Fatty acyl Alkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative Amino acid or derivatives Amino acid Carboxylic acid ester Carboxylic acid derivative Carboxylic acid Organooxygen compound Organic nitrogen compound Primary amine Carbonyl group Hydrocarbon derivative Organic oxide Amine Organic oxygen compound Primary aliphatic amine Organonitrogen compound Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic 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 0.00018 g/L ALOGPS logP 3.59 ALOGPS logP 7.38 ChemAxon logS -6.6 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 35 ChemAxon Refractivity 181.12 m³·mol⁻¹ ChemAxon Polarizability 80.28 ų ChemAxon Number of Rings 1 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(19:0cycw8c/10:0) + L-Serine + L-Serine > PS(19:0cycw8c/10:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PS(19:0cycw8c/10:0) + Hydrogen ion > PE(19:0cycw8c/10:0) + Carbon dioxide
SMPDB Pathways:	phospholipid biosynthesis (CL(19:0cycw8c/10:0/10:0/10:0)) PW001994
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_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative Not Available View in JSpectraViewer MS Mass Spectrum (Electron Ionization) 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 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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