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Showing Compound PS(16:0/16:0) (FDB022144)

Record Information
Version1.0
Creation date2011-09-21 00:09:07 UTC
Update date2020-04-06 23:43:34 UTC
Primary IDFDB022144
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePS(16:0/16:0)
DescriptionPS(16:0/16:0) 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 positions. PS(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. 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.
CAS Number3036-82-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,2-Dipalmitoyl-sn-glycero-3-phosphoserineChEBI
1,2-DipalmitoylglycerophosphorylserineChEBI
Phosphatidylserine (16:0/16:0)ChEBI
pSer(16:0/16:0)ChEBI
PS(32:0)HMDB
Phosphatidylserine(16:0/16:0)HMDB
1,2-Dipalmitoyl-rac-glycero-3-phosphoserineHMDB
pSer(32:0)HMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphoserineHMDB
Phosphatidylserine(32:0)HMDB
DPPSHMDB
DipalmitoylphosphatidylserineHMDB
1,2-Dipalmitoyl-GPSHMDB
1,2-Dipalmitoyl-sn-3-glycerophosphoserineHMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphatidylserineHMDB
1,2-Dipalmitoyl-sn-glycero-3-phospho-L-serineHMDB
Dipalmitoyl-sn-glycerol-3-phosphorylserineHMDB
L-alpha-DipalmitoylphosphatidylserineHMDB
L-Α-dipalmitoylphosphatidylserineHMDB
PS(16:0/16:0)Lipid Annotator, ChEBI
1,2-DipalmitoylatidylserineHMDB
1,2-DipalmitoylglyceroorylserineHMDB
1,2-Dipalmitoylphosphatidylserinehmdb
Atidylserine (16:0/16:0)HMDB
Atidylserine (32:0)HMDB
Dipalmitoyl-DL-a-atidyl-L-serineHMDB
Dipalmitoyl-DL-a-phosphatidyl-L-serinehmdb
Dipalmitoyl-DL-alpha-atidyl-L-serineHMDB
Dipalmitoyl-DL-alpha-phosphatidyl-L-serinehmdb
DipalmitoylatidylserineHMDB
DipalmitoylglycerooserineHMDB
Dipalmitoylglycerophosphoserinehmdb
DL-a-Dipalmitoyl atidyl-L-serineHMDB
DL-a-Dipalmitoyl phosphatidyl-L-serinehmdb
DL-alpha-Dipalmitoyl atidyl-L-serineHMDB
DL-alpha-Dipalmitoyl phosphatidyl-L-serinehmdb
Phosphatidylserine (32:0)hmdb
PSer(16:0/16:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0001 g/LALOGPS
logP4.32ALOGPS
logP9.49ChemAxon
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 Count40ChemAxon
Refractivity196.83 m³·mol⁻¹ChemAxon
Polarizability88.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC38H74NO10P
IUPAC name(2S)-2-amino-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
InChI IdentifierInChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34-,35+/m1/s1
InChI KeyKLFKZIQAIPDJCW-GPOMZPHUSA-N
Isomeric SMILES[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(O)=O
Average Molecular Weight735.981
Monoisotopic Molecular Weight735.505034585
Classification
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
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPS(16:0/16:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(16:0/16:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(16:0/16:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(16:0/16:0), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(16:0/16:0), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(16:0/16:0), TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0000393000-5d82d8d3c3cc3a8e1ef72016-09-19View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0000016900-6bb9b6bacde6d8b4611b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000002900-eaf2a2217a8f79f1c16c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090033100-708416ca737a3b1fee062021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000010900-db7bc8c2e3b9dad9960c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0001391600-51c373de4449f596bd5c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001391100-9a4a9ad709f158064e082021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-14i6-0000099900-38c346454df0c2d55b3a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0900099900-cf1ed9c46228bdf4f23f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-0900099900-cf1ed9c46228bdf4f23f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-402c44be8653ebc0c2842021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000001900-2b5ae18fbcabd46b8f692021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-0166109600-e8d10538897e7b62801e2021-09-24View Spectrum
NMRNot Available
ChemSpider ID2338998
ChEMBL IDNot Available
KEGG Compound IDC02737
Pubchem Compound ID3081382
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00614
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Phosphatidylserine synthase 1PTDSS1P48651
Phosphatidylserine synthase 2PTDSS2Q9BVG9
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL1O15357
Scavenger receptor class B member 1SCARB1Q8WTV0
Phospholipase A1 member APLA1AQ53H76
Protein kinase C delta-binding proteinPRKCDBPQ969G5
LactadherinMFGE8Q08431
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025 map00564
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference