Record Information
Version1.0
Creation date2011-09-21 01:48:36 UTC
Update date2016-06-28 20:14:07 UTC
Primary IDFDB029001
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePS(18:1(9Z)/14:0)
DescriptionPS(18:1(9Z)/14:0) 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(18:1(9Z)/14:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one tetradecanoyl 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.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Oleoyl-2-myristoyl-sn-glycero-3-oserineHMDB
1-oleoyl-2-myristoyl-sn-glycero-3-phosphoserinehmdb
Atidylserine(18:1/14:0)HMDB
Atidylserine(18:1N9/14:0)HMDB
Atidylserine(18:1W9/14:0)HMDB
Phosphatidylserine(18:1/14:0)hmdb
Phosphatidylserine(18:1n9/14:0)hmdb
Phosphatidylserine(18:1w9/14:0)hmdb
PS(18:1/14:0)hmdb
PS(18:1n9/14:0)hmdb
PS(18:1w9/14:0)hmdb
PSer(18:1/14:0)hmdb
PSer(18:1n9/14:0)hmdb
PSer(18:1w9/14:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP4.3ALOGPS
logP9.13ChemAxon
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
Refractivity197.95 m³·mol⁻¹ChemAxon
Polarizability87.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC38H72NO10P
IUPAC name(2S)-2-amino-3-({hydroxy[(2R)-3-(octadec-9-enoyloxy)-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
InChI IdentifierInChI=1S/C38H72NO10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-19-14-12-10-8-6-4-2/h16-17,34-35H,3-15,18-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34-,35+/m1/s1
InChI KeyHEKHACWHBXMEFM-GPOMZPHUSA-N
Isomeric SMILES[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=O
Average Molecular Weight733.9527
Monoisotopic Molecular Weight733.489384041
Classification
ClassificationNot classified
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
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID52925991
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12385
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference