Record Information
Version1.0
Creation date2011-09-21 01:48:38 UTC
Update date2016-06-28 20:14:08 UTC
Primary IDFDB029003
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePS(18:1(9Z)/16:0)
DescriptionPS(18:1(9Z)/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 atoms. PS(18:1(9Z)/16:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one hexadecanoyl 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-(9Z)-Octadecenoyl-2-hexadecanoyl-sn-glycero-3-phospho-L-serineChEBI
1-(9Z-Octadecenoyl)-2-hexadecanoyl-glycero-3-phosphoserineChEBI
1-C18:1(Omega-9)-2-C16:0-phosphatidylserineChEBI
1-Oleoyl-2-palmitoyl-sn-glycero-3-phosphoserineChEBI
O-{hydroxy[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(palmitoyloxy)propoxy]phosphoryl}-L-serineChEBI
Phosphatidylserine(18:1omega9/16:0)ChEBI
Phosphatidylserine(34:1)ChEBI
PS(18:1/16:0)ChEBI
PS(18:1OMEGA9/16:0)ChEBI
PS(34:1)ChEBI
Phosphatidylserine(18:1/16:0)HMDB
Phosphatidylserine(18:1n9/16:0)HMDB
Phosphatidylserine(18:1W9/16:0)HMDB
PS(18:1N9/16:0)HMDB
PS(18:1W9/16:0)HMDB
pSer(18:1/16:0)HMDB
pSer(18:1n9/16:0)HMDB
pSer(18:1W9/16:0)HMDB
pSer(34:1)HMDB
1-(9Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoserineHMDB
PS(18:1(9Z)/16:0)Lipid Annotator
1-Oleoyl-2-palmitoyl-sn-glycero-3-oserineHMDB
1-oleoyl-2-palmitoyl-sn-glycero-3-phosphoserinehmdb
Atidylserine(18:1/16:0)HMDB
Atidylserine(18:1N9/16:0)HMDB
Atidylserine(18:1W9/16:0)HMDB
Phosphatidylserine(18:1w9/16:0)hmdb
PS(18:1n9/16:0)hmdb
PS(18:1w9/16:0)hmdb
PSer(18:1/16:0)hmdb
PSer(18:1n9/16:0)hmdb
PSer(18:1w9/16:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility8.5e-05 g/LALOGPS
logP4.64ALOGPS
logP10.02ChemAxon
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 Count41ChemAxon
Refractivity207.15 m³·mol⁻¹ChemAxon
Polarizability90.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H76NO10P
IUPAC name(2S)-2-amino-3-({[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
InChI IdentifierInChI=1S/C40H76NO10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-38(42)48-33-36(34-49-52(46,47)50-35-37(41)40(44)45)51-39(43)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h17-18,36-37H,3-16,19-35,41H2,1-2H3,(H,44,45)(H,46,47)/b18-17-/t36-,37+/m1/s1
InChI KeyILJAXXNZNFOOQA-DAQGAKHBSA-N
Isomeric SMILES[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(O)=O
Average Molecular Weight762.019
Monoisotopic Molecular Weight761.520684649
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9040110300-9d419fa497cad9d214dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000000-4e40c3900101172f60ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9152002000-5e4c2d6ef850233fd7fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-1190011200-105cce0822b757b2bbcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4290000000-f1541820ee2d0629c304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030100000-c61a5e60dd2cf6b8b144View in MoNA
ChemSpider ID29368496
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID52926066
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12387
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference