Record Information
Version2.0
Creation Date2012-05-31 14:55:34 -0600
Update Date2015-12-09 17:00:41 -0700
Secondary Accession Numbers
  • ECMDB21036
Identification
Name:PS(14:0/17:0)
DescriptionPS(14:0/17:0) 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(14:0/17:0), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one heptadecanoyl 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:
  • 1-myristoyl-2-heptadecanoyl-sn-glycero-3-phosphoserine
  • 1-tetradecanoyl-2-heptadecanoyl-glycero-3-phosphoserine
  • 1-tetradecanoyl-2-margaroyl-sn-glycero-3-phosphoserine
  • Phosphatidylserine(14:0/17:0)
  • Phosphatidylserine(31:0)
  • PS(31:0)
  • PSer(14:0/17:0)
  • PSer(31:0)
Chemical Formula:C37H72NO10P
Weight:Average: 721.954
Monoisotopic: 721.48938452
InChI Key:PJCUMCRIZXYQCZ-KKLWWLSJSA-N
InChI:InChI=1S/C37H72NO10P/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-36(40)48-33(31-46-49(43,44)47-32-34(38)37(41)42)30-45-35(39)28-26-24-22-20-18-14-12-10-8-6-4-2/h33-34H,3-32,38H2,1-2H3,(H,41,42)(H,43,44)/t33-,34-/m1/s1
CAS number:Not Available
IUPAC Name:(2R)-2-amino-3-({[(2R)-2-(heptadecanoyloxy)-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name:(2R)-2-amino-3-{[(2R)-2-(heptadecanoyloxy)-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
SMILES:[H][C@@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC)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.
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
  • 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00013 g/LALOGPS
logP4.14ALOGPS
logP9.05ChemAxon
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 Count39ChemAxon
Refractivity192.23 m³·mol⁻¹ChemAxon
Polarizability85.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/17:0cycw7c))PW001667 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/17:0cycw7c))PW001436 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/14:0))PW001444 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/14:0/14:0)PW001031 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/14:0/16:0)PW001032 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/14:0/16:1(9Z))PW001871 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/16:1(9Z)/14:0)PW001036 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/14:0/17:0cycw7c/14:0)PW001055 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/14:0/14:0)PW001204 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/14:0/16:1(9Z))PW001206 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/16:1(9Z)/14:0)PW001213 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/14:0/17:0cycw7c)PW001254 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/17:0cycw7c/14:0)PW001270 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/17:0cycw7c/14:0/16:0)PW001338 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/17:0cycw7c/16:0/14:0)PW001342 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/18:1(9Z)/18:1(9Z))PW001427 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/16:1(9Z))PW001513 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/17:0cycw7c)PW001520 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/14:0)PW001523 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/14:0)PW001535 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/14:0/16:1(9Z))PW001558 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/16:1(9Z)/14:0)PW001560 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/18:1(9Z))PW001573 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(17:0cycw7c/16:0/14:0/16:0)PW001663 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(17:0cycw7c/16:0/16:0/14:0)PW001675 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(17:0cycw7c/16:1(9Z)/14:0/16:1(9Z))PW001693 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_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9040200200-e5239cbdcc081b4efa06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9020000000-30076175117e07ac8267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9150021000-12b9a630cb729cec0413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0l4i-1190201200-26724b722b4517e256c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5390100000-60b19c8b8c8ceef15504View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-bc909597a76d459d614fView 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:
  • 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
  • Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
  • 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

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:
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