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Record Information
StatusDetected and Quantified
Creation Date2009-06-16 18:12:03 UTC
Update Date2020-02-26 21:37:29 UTC
Secondary Accession Numbers
  • HMDB12390
Metabolite Identification
Common NamePS(18:1(9Z)/18:1(9Z))
DescriptionPS(18:1(9Z)/18:1(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(18:1(9Z)/18:1(9Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of oleic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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.
Dioleoyl phosphatidylserineChEBI
1,2-Dioleoylphosphatidylserine, monosodium salt, (R-(Z,Z))-isomerHMDB
1,2-Dioleoylphosphatidylserine, sodium salt, (Z,Z)-isomerHMDB
1,2-Dioleoylphosphatidylserine, (Z,Z)-isomerHMDB
PS(18:1(9Z)/18:1(9Z))Lipid Annotator
Chemical FormulaC42H78NO10P
Average Molecular Weight788.057
Monoisotopic Molecular Weight787.536334714
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional NameDOPS
CAS Registry NumberNot Available
InChI Identifier
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
Sub ClassGlycerophosphoserines
Direct ParentPhosphatidylserines
Alternative Parents
  • 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
Physiological effect

Organoleptic effect:


Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility7.1e-05 g/LALOGPS
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 Count42ChemAxon
Refractivity217.47 m³·mol⁻¹ChemAxon
Polarizability93.32 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-015a-0130905000-d8f46442e4e3c7adefb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-014i-0000000900-cf40d0ddb17ab7974b2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-014i-0010000900-aadf954c64f212ee11f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-016r-0040000900-d7953ea3372a35e684abSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-00or-0090000700-0715d812928b42a7715bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-004i-0090000100-ce0d176424e9c1a4f9fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 80V, negativesplash10-004i-0090000000-f158e209a254a9ce3737Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 97V, negativesplash10-004i-0090000000-71551f9569be509f99aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 119V, negativesplash10-004i-1190000000-9ed3d13d5b84f65074cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 141V, negativesplash10-004i-7390000000-9f14978138420782a4feSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 173V, negativesplash10-004i-9100000000-da1c2f0fd31c179420bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004i-0090210000-757499483c20b79dd5d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004i-0090000000-cd763c6dcf40c4ec2356Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-06r6-1190000000-ba930116c1335ab330bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004i-0090000000-52430f6dfd091c56b260Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004j-9000000000-44c080f0b731402e500cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-000i-0000000900-1c12b250e6fed3ac7e0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000j-0000407900-9030c795256b7df30091Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, negativesplash10-014i-1030903000-e20c6f02695a38934804Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9020120400-98e01c33f1aa8610b08dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9010000000-f9f138a277fa485d97c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9023011100-8497477243b05d931f5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-1190132300-8af751ae39bd84c631a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390110000-38da08ecdf851290d577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120100000-cf3378ec40f70542a26dSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • All Tissues
  • Brain
  • Heart
  • Kidney
  • Liver
Normal Concentrations
BloodDetected and Quantified0.316 +/- 0.065 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029006
KNApSAcK IDNot Available
Chemspider ID4943103
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438639
ChEBI ID60568
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  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. [PubMed:9450519 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  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. [PubMed:22960354 ]
  8. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  10. Jean E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. The Journal of Lipid Research, 49, 1377-1387..

Only showing the first 10 proteins. There are 41 proteins in total.


General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:
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Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in diacylglycerol kinase activity
Specific function:
Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in protein serine/threonine kinase activity
Specific function:
PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in calcium ion binding
Specific function:
May play a role in the antiviral response of interferon (IFN) by amplifying and enhancing the IFN response through increased expression of select subset of potent antiviral genes. May contribute to cytokine-regulated cell proliferation and differentiation
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in phosphatidylserine biosynthetic process
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in cell adhesion
Specific function:
Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
Gene Name:
Uniprot ID:
Molecular weight:

Only showing the first 10 proteins. There are 41 proteins in total.