Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB006723
Identification
Name: PS(16:0/19:0cycw8c)
Description:PS(16:0/19:0cycw8c) 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(16:0/19:0cycw8c), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9-(2-heptylcyclopropyl)nonanoyl 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
Thumb
Synonyms:Not Available
Chemical Formula: C41H78NO10P
Average Molecular Weight: 776.046
Monoisotopic Molecular Weight: 775.536334714
InChI Key: MFZARXRTFPJNNA-KBTHPEDISA-N
InChI:InChI=1S/C41H78NO10P/c1-3-5-7-9-10-11-12-13-14-15-16-21-25-29-39(43)49-32-37(33-50-53(47,48)51-34-38(42)41(45)46)52-40(44)30-26-22-18-17-20-24-28-36-31-35(36)27-23-19-8-6-4-2/h35-38H,3-34,42H2,1-2H3,(H,45,46)(H,47,48)/t35?,36?,37-,38+/m1/s1
CAS number: Not Available
IUPAC Name:(2S)-2-amino-3-({[(2R)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name: (2S)-2-amino-3-{[(2R)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
SMILES:[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC1CC1CCCCCCC)C(O)=O
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
  • 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:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.94e-05 mg/mLALOGPS
logP4.7ALOGPS
logP10.05ChemAxon
logS-7.1ALOGPS
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 Count41ChemAxon
Refractivity208.73 m3·mol-1ChemAxon
Polarizability91.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways: Not Available
Spectra
Spectra:
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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available