PS(14:0/14:0) (CHEM040788)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:34:08 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040788
Identification
Common NamePS(14:0/14:0)
ClassSmall Molecule
DescriptionPS(14:0/14:0), also known as ps(14:0/14:0) or PS(28:0), 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. Thus, PS(14:0/14:0) is considered to be a glycerophosphoserine lipid molecule. PS(14:0/14:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(14:0/14:0) exists in all eukaryotes, ranging from yeast to humans. PS(14:0/14:0) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(14:0/14:0) can be biosynthesized from PC(14:0/14:0) and L-serine through the action of the enzyme phosphatidylserine synthase. In addition, PS(14:0/14:0) can be converted into PE(14:0/14:0); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(14:0/14:0) is involved in the metabolic pathway called phosphatidylethanolamine biosynthesis pe(14:0/14:0) pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PSer(14:0/14:0)Lipid Annotator, HMDB
PS(14:0/14:0)Lipid Annotator
1,2-dimyristoyl-rac-glycero-3-phosphoserineLipid Annotator, HMDB
Phosphatidylserine(28:0)Lipid Annotator, HMDB
PSer(28:0)Lipid Annotator, HMDB
Phosphatidylserine(14:0/14:0)Lipid Annotator, HMDB
1,2-ditetradecanoyl-rac-glycero-3-phosphoserineLipid Annotator, HMDB
PS(28:0)Lipid Annotator, HMDB
1-Myristoyl-2-myristoyl-sn-glycero-3-phosphoserineHMDB
1,2-Dimyristoyl-sn-glycero-3-phosphorylserineMeSH, HMDB
DMPSEMeSH, HMDB
DimyristoylphosphatidylserineMeSH
Chemical FormulaC34H66NO10P
Average Molecular Mass679.873 g/mol
Monoisotopic Mass679.442 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Namedimyristoyl phosphatidylserine
SMILES[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=O
InChI IdentifierInChI=1S/C34H66NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(36)42-27-30(28-43-46(40,41)44-29-31(35)34(38)39)45-33(37)26-24-22-20-18-16-14-12-10-8-6-4-2/h30-31H,3-29,35H2,1-2H3,(H,38,39)(H,40,41)/t30-,31+/m1/s1
InChI KeyWKJDWDLHIOUPPL-JSOSNVBQSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP3.54ALOGPS
logP7.72ChemAxon
logS-6.5ALOGPS
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 Count36ChemAxon
Refractivity178.43 m³·mol⁻¹ChemAxon
Polarizability79.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9020504000-fa65692295f5adcc7ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9110200000-b504718afbcbea8ecff5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9240011000-a087983d8e44efefed84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-2190324000-7138b794823e340d5229Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5491211000-6f92e677f8423e495c74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9111000000-fba84b7bb1fc13e2c78eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0000999000-3e9d84352749b134f12eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000e-0900999000-0113e536da6bee3ddcfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000e-0900999000-0113e536da6bee3ddcfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000009000-54f908a64f8a9e5c5497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000019000-a6ed6050fc32085c29c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tc-0167096000-f5cf7b7584411ef6d360Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000106900-aff251d6c4c2b1919331Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000002900-4272577249d187603017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090113100-a000ef32c316df2f3517Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000109000-1a8d3f2f81603500cfdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0010914000-1c83cbac7d02b25a22b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0010911000-36d8bb91cf577de13157Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012330
FooDB IDFDB028949
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110272
ChEBI IDNot Available
PubChem Compound ID123699
Kegg Compound IDNot Available
YMDB IDYMDB15484
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
2. van Engeland M, Nieland LJ, Ramaekers FC, Schutte B, Reutelingsperger CP: Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry. 1998 Jan 1;31(1):1-9.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Vance JE, Tasseva G: Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells. Biochim Biophys Acta. 2013 Mar;1831(3):543-54. doi: 10.1016/j.bbalip.2012.08.016. Epub 2012 Aug 29.
8. Phospholipids Handbook
9. The lipid handbook with CD-ROM
10. Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids