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PS(18:0/18:1(9Z)) (YMDB01257)

Identification
YMDB IDYMDB01257
NamePS(18:0/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPS(18:0/18:1(9Z)) 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(18:0/18:1(9Z)), in particular, consists of one octadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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
MOLSDFPDBSMILESInChI
Synonyms
  • 1-D-phosphatidyl-L-serine
  • 1-stearoyl-2-oleoyl-sn-glycero-3-phosphoserine
  • 1,2-Diacyl-sn-glycerol 3-phospho-L-serine
  • 3-L-phosphatidyl-L-serine
  • 3-O-sn-Phosphatidyl-L-serine
  • 3-sn-phosphatidyl-L-serines
  • L-alpha-phosphatidylserine
  • O3-Phosphatidyl-L-serine
  • Phosphatidyl-L-serine
  • Phosphatidylserine
  • Phosphatidylserine(18:0/18:1)
  • Phosphatidylserine(18:0/18:1n9)
  • Phosphatidylserine(18:0/18:1w9)
  • Phosphatidylserine(36:1)
  • PS(18:0/18:1)
  • PS(18:0/18:1n9)
  • PS(18:0/18:1w9)
  • PS(36:1)
  • PSer(18:0/18:1)
  • PSer(18:0/18:1n9)
  • PSer(18:0/18:1w9)
  • PSer(36:1)
  • 1-18:0-2-18:1-Phosphatidylserine
  • 1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoserine
  • 1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoserine
  • 18:0-18:1-PS
  • O-{hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(stearoyloxy)propoxy]phosphoryl}-L-serine
  • Phosphatidyl-L-serine (1-18:0-2-18:1)
  • 1-Stearoyl-2-oleoyl-GPS
  • Phosphatidylserine(18:0/18:1(9Z))
  • pSer(18:0/18:1(9Z))
  • PS(18:0/18:1(9Z))
CAS numberNot Available
WeightAverage: 790.073
Monoisotopic: 789.551984778
InChI KeyAJFWREUFUPEYII-PAHWMLEVSA-N
InChIInChI=1S/C42H80NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h18,20,38-39H,3-17,19,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b20-18-/t38-,39+/m1/s1
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional IUPAC Name(2S)-2-amino-3-{[hydroxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphoryl]oxy}propanoic acid
Chemical FormulaC42H80NO10P
SMILES[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)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. 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.
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
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.1e-05 g/LALOGPS
logP4.95ALOGPS
logP10.91ChemAxon
logS-7ALOGPS
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 Count43ChemAxon
Refractivity216.35 m³·mol⁻¹ChemAxon
Polarizability94.89 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycine, serine and threonine metabolismec00260 Map00260
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9020120400-8b3abf5ee490081655e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9010000000-6b12a96913918691d068JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9033011100-c3cb36db3c464cb00b34JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1190030400-c27322c37aa82f6bfec3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390110100-2b169a92a9dd7bbe9b3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120100000-004f297a75be7d9fe009JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-92358d2708fbe52da6aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0003069700-0b11fc1d31df804fe9bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003069300-1f2b15ffbc23b6d8895cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0000004900-8ddd472a449c7238e6d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4m-0400004900-d50ddf3988d0dcf20378JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-0400004900-d50ddf3988d0dcf20378JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-fe622cdc999efc524fd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000900-a50108dabb7bd3623c4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gd0-0070900800-281b84595f9bb7100373JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0000001690-dab1e81094b582889f19JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000290-ec13b6db523d0d9d58ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-37d350319f45448a6c64JSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID11750
HMDB IDHMDB10163
Pubchem Compound ID3451126
Kegg IDC02737
ChemSpider ID7826037
FOODB IDFDB027346
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-SERINE