Record Information
Version3.6
Creation Date2009-06-16 18:11:05 UTC
Update Date2013-02-09 00:28:50 UTC
HMDB IDHMDB12333
Secondary Accession NumbersNone
Metabolite Identification
Common NamePS(14:0/16:1(9Z))
DescriptionPS(14:0/16:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:0/16:1(9Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. 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, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. 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
Synonyms
  1. 1-Myristoyl-2-palmitoleoyl-sn-glycero-3-phosphoserine
  2. Phosphatidylserine(14:0/16:1)
  3. Phosphatidylserine(14:0/16:1n7)
  4. Phosphatidylserine(14:0/16:1w7)
  5. Phosphatidylserine(30:1)
  6. PS(14:0/16:1)
  7. PS(14:0/16:1n7)
  8. PS(14:0/16:1w7)
  9. PS(30:1)
  10. PSer(14:0/16:1)
  11. PSer(14:0/16:1n7)
  12. PSer(14:0/16:1w7)
  13. PSer(30:1)
Chemical FormulaC36H68NO10P
Average Molecular Weight705.8996
Monoisotopic Molecular Weight705.458083913
IUPAC Name(2S)-2-amino-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name(2S)-2-amino-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)C(O)=O
InChI Identifier
InChI=1S/C36H68NO10P/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-35(39)47-32(30-45-48(42,43)46-31-33(37)36(40)41)29-44-34(38)27-25-23-21-19-17-14-12-10-8-6-4-2/h13,15,32-33H,3-12,14,16-31,37H2,1-2H3,(H,40,41)(H,42,43)/b15-13-/t32-,33+/m1/s1
InChI KeyDPYXPLKOAXFWHZ-BKTZGLHTSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphoserines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Alpha Amino Acid Or Derivative
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
  • Tricarboxylic Acid Derivative
Direct ParentPhosphatidylserines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility1.530E-04 g/LALOGPS
logP3.93ALOGPS
logP8.24ChemAxon
logS-6.7ALOGPS
pKa (strongest acidic)1.47ChemAxon
pKa (strongest basic)9.38ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count3ChemAxon
polar surface area171.68ChemAxon
rotatable bond count37ChemAxon
refractivity188.75ChemAxon
polarizability82.09ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
  • Brain
  • Heart
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028952
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12333
Metagene LinkHMDB12333
METLIN IDNot Available
PubChem Compound52926036
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
PLA2G10
Uniprot ID:
O15496
Gene Name:
DGKG
Uniprot ID:
P49619
Gene Name:
DGKA
Uniprot ID:
P23743
Gene Name:
DGKD
Uniprot ID:
Q16760
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Gene Name:
PRKCA
Uniprot ID:
P17252
Gene Name:
PLSCR1
Uniprot ID:
O15162
Gene Name:
PTDSS1
Uniprot ID:
P48651
Gene Name:
SCARB1
Uniprot ID:
Q8WTV0
Gene Name:
CXCL16
Uniprot ID:
Q9H2A7
Gene Name:
PTDSS2
Uniprot ID:
Q9BVG9
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Gene Name:
SMPD3
Uniprot ID:
Q9NY59
Gene Name:
PLSCR2
Uniprot ID:
Q9NRY7
Gene Name:
PLSCR3
Uniprot ID:
Q9NRY6
Gene Name:
PLSCR4
Uniprot ID:
Q9NRQ2
Gene Name:
PLSCR5
Uniprot ID:
A0PG75
Gene Name:
PLA1A
Uniprot ID:
Q53H76
Gene Name:
SDPR
Uniprot ID:
O95810
Gene Name:
ATRX
Uniprot ID:
P46100
Gene Name:
CPNE1
Uniprot ID:
Q99829
Gene Name:
CPNE6
Uniprot ID:
O95741
Gene Name:
TRIP10
Uniprot ID:
Q15642
Gene Name:
FNBP1L
Uniprot ID:
Q5T0N5
Gene Name:
FNBP1
Uniprot ID:
Q96RU3
Gene Name:
SMPD4
Uniprot ID:
Q9NXE4
Gene Name:
SERINC1
Uniprot ID:
Q9NRX5
Gene Name:
PRKCDBP
Uniprot ID:
Q969G5
Gene Name:
ANXA9
Uniprot ID:
O76027
Gene Name:
SERINC5
Uniprot ID:
Q86VE9
Gene Name:
SCIN
Uniprot ID:
Q9Y6U3
Gene Name:
SERINC4
Uniprot ID:
A6NH21
Gene Name:
MFGE8
Uniprot ID:
Q08431