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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:48 UTC
Update Date2020-02-26 21:39:24 UTC
Secondary Accession Numbers
  • HMDB14291
Metabolite Identification
Common NamePhosphatidylserine
DescriptionPhosphatidylserine (PS) is a phospholipid nutrient found in fish, green leafy vegetables, soybeans and rice, and is essential for the normal functioning of neuronal cell membranes and activates Protein kinase C (PKC) which has been shown to be involved in memory function. In apoptosis, phosphatidylserine is transferred to the outer leaflet of the plasma membrane. This is part of the process by which the cell is targeted for phagocytosis. PS has been shown to slow cognitive decline in animal models. PS has been investigated in a small number of double-blind placebo trials and has been shown to increase memory performance in the elderly. Because of the potentail cognitive benefits of phosphatidylserine, the substance is sold as a dietary supplement to people who believe they can benefit from an increased intake. The dietary supplement was originally processed from bovine sources however Prion disease scares in the 1990s outlawed this process, and a soy-based alternative was adopted.
Chemical FormulaC13H24NO10P
Average Molecular Weight385.3041
Monoisotopic Molecular Weight385.113782505
IUPAC Name(2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Namephosphatidylserine
CAS Registry Number8002-43-5
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 DescriptorsNot Available
Physiological effect

Organoleptic effect:


Route of exposure:


Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.7 g/LNot Available
LogP-3.5Not Available
Predicted Properties
Water Solubility3.7 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 Count15ChemAxon
Refractivity81.81 m³·mol⁻¹ChemAxon
Polarizability35.59 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06xx-9331000000-5397fe5806bdc09af389Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9125000000-a42f2f526549a4b9fc5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9013000000-a48d79654fdd42e7b832Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9010000000-3e5d23a16d25de896747Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9200000000-a15a472f35148d4c5da0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9123000000-667f29964b87dbc7f6bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-9110000000-798e4cca9186bc74d867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a8525ea4757be1346489Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00144 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00144 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00144
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13628254
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhosphatidylserine
METLIN IDNot Available
PubChem Compound6323481
PDB IDNot Available
ChEBI ID18303
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..


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:
  1. Yamaguchi Y, Shirai Y, Matsubara T, Sanse K, Kuriyama M, Oshiro N, Yoshino K, Yonezawa K, Ono Y, Saito N: Phosphorylation and up-regulation of diacylglycerol kinase gamma via its interaction with protein kinase C gamma. J Biol Chem. 2006 Oct 20;281(42):31627-37. Epub 2006 Aug 11. [PubMed:16905533 ]
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:
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  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Bregoli L, Baldassare JJ, Raben DM: Nuclear diacylglycerol kinase-theta is activated in response to alpha-thrombin. J Biol Chem. 2001 Jun 29;276(26):23288-95. Epub 2001 Apr 17. [PubMed:11309392 ]
  4. Sakane F, Imai S, Kai M, Wada I, Kanoh H: Molecular cloning of a novel diacylglycerol kinase isozyme with a pleckstrin homology domain and a C-terminal tail similar to those of the EPH family of protein-tyrosine kinases. J Biol Chem. 1996 Apr 5;271(14):8394-401. [PubMed:8626538 ]
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:
  1. Yu D, Kazanietz MG, Harvey RG, Penning TM: Polycyclic aromatic hydrocarbon o-quinones inhibit the activity of the catalytic fragment of protein kinase C. Biochemistry. 2002 Oct 1;41(39):11888-94. [PubMed:12269833 ]
  2. Rodriguez-Alfaro JA, Gomez-Fernandez JC, Corbalan-Garcia S: Role of the lysine-rich cluster of the C2 domain in the phosphatidylserine-dependent activation of PKCalpha. J Mol Biol. 2004 Jan 23;335(4):1117-29. [PubMed:14698304 ]
  3. Lopez-Andreo MJ, Torrecillas A, Conesa-Zamora P, Corbalan-Garcia S, Gomez-Fernandez JC: Retinoic acid as a modulator of the activity of protein kinase Calpha. Biochemistry. 2005 Aug 30;44(34):11353-60. [PubMed:16114872 ]
  4. Corbin JA, Evans JH, Landgraf KE, Falke JJ: Mechanism of specific membrane targeting by C2 domains: localized pools of target lipids enhance Ca2+ affinity. Biochemistry. 2007 Apr 10;46(14):4322-36. Epub 2007 Mar 17. [PubMed:17367165 ]
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:
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Molecular weight:
  1. Bettache N, Baisamy L, Baghdiguian S, Payrastre B, Mangeat P, Bienvenue A: Mechanical constraint imposed on plasma membrane through transverse phospholipid imbalance induces reversible actin polymerization via phosphoinositide 3-kinase activation. J Cell Sci. 2003 Jun 1;116(Pt 11):2277-84. Epub 2003 Apr 15. [PubMed:12697835 ]
  2. Wolfs JL, Comfurius P, Rasmussen JT, Keuren JF, Lindhout T, Zwaal RF, Bevers EM: Activated scramblase and inhibited aminophospholipid translocase cause phosphatidylserine exposure in a distinct platelet fraction. Cell Mol Life Sci. 2005 Jul;62(13):1514-25. [PubMed:15971000 ]
  3. Mandal D, Mazumder A, Das P, Kundu M, Basu J: Fas-, caspase 8-, and caspase 3-dependent signaling regulates the activity of the aminophospholipid translocase and phosphatidylserine externalization in human erythrocytes. J Biol Chem. 2005 Nov 25;280(47):39460-7. Epub 2005 Sep 22. [PubMed:16179347 ]
  4. Paterson JK, Renkema K, Burden L, Halleck MS, Schlegel RA, Williamson P, Daleke DL: Lipid specific activation of the murine P4-ATPase Atp8a1 (ATPase II). Biochemistry. 2006 Apr 25;45(16):5367-76. [PubMed:16618126 ]
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:
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Molecular weight:
  1. Kuge O, Nishijima M: Biosynthetic regulation and intracellular transport of phosphatidylserine in mammalian cells. J Biochem. 2003 Apr;133(4):397-403. [PubMed:12761285 ]
  2. Kuge O, Hasegawa K, Ohsawa T, Saito K, Nishijima M: Purification and characterization of Chinese hamster phosphatidylserine synthase 2. J Biol Chem. 2003 Oct 24;278(43):42692-8. Epub 2003 Aug 11. [PubMed:12912985 ]
  3. Ohsawa T, Nishijima M, Kuge O: Functional analysis of Chinese hamster phosphatidylserine synthase 1 through systematic alanine mutagenesis. Biochem J. 2004 Aug 1;381(Pt 3):853-9. [PubMed:15130088 ]
  4. Steenbergen R, Nanowski TS, Nelson R, Young SG, Vance JE: Phospholipid homeostasis in phosphatidylserine synthase-2-deficient mice. Biochim Biophys Acta. 2006 Mar;1761(3):313-23. Epub 2006 Mar 31. [PubMed:16627002 ]
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:
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Molecular weight:
  1. Yan X, Poelstra K, Scherphof GL, Kamps JA: A role for scavenger receptor B-I in selective transfer of rhodamine-PE from liposomes to cells. Biochem Biophys Res Commun. 2004 Dec 17;325(3):908-14. [PubMed:15541376 ]
  2. Yancey PG, Kawashiri MA, Moore R, Glick JM, Williams DL, Connelly MA, Rader DJ, Rothblat GH: In vivo modulation of HDL phospholipid has opposing effects on SR-BI- and ABCA1-mediated cholesterol efflux. J Lipid Res. 2004 Feb;45(2):337-46. Epub 2003 Nov 1. [PubMed:14594995 ]
  3. Nakagawa A, Shiratsuchi A, Tsuda K, Nakanishi Y: In vivo analysis of phagocytosis of apoptotic cells by testicular Sertoli cells. Mol Reprod Dev. 2005 Jun;71(2):166-77. [PubMed:15791597 ]
  4. Zhang J, Fujii S, Wu Z, Hashioka S, Tanaka Y, Shiratsuchi A, Nakanishi Y, Nakanishi H: Involvement of COX-1 and up-regulated prostaglandin E synthases in phosphatidylserine liposome-induced prostaglandin E2 production by microglia. J Neuroimmunol. 2006 Mar;172(1-2):112-20. Epub 2005 Dec 20. [PubMed:16371234 ]
  5. Osada Y, Shiratsuchi A, Nakanishi Y: Involvement of mitogen-activated protein kinases in class B scavenger receptor type I-induced phagocytosis of apoptotic cells. Exp Cell Res. 2006 Jun 10;312(10):1820-30. Epub 2006 Mar 10. [PubMed:16530182 ]
General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Not Available
Gene Name:
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Molecular weight:
  1. Wu WI, Voelker DR: Reconstitution of phosphatidylserine transport from chemically defined donor membranes to phosphatidylserine decarboxylase 2 implicates specific lipid domains in the process. J Biol Chem. 2004 Feb 20;279(8):6635-42. Epub 2003 Dec 4. [PubMed:14660568 ]
  2. Burgermeister M, Birner-Grunberger R, Heyn M, Daum G: Contribution of different biosynthetic pathways to species selectivity of aminoglycerophospholipids assembled into mitochondrial membranes of the yeast Saccharomyces cerevisiae. Biochim Biophys Acta. 2004 Nov 8;1686(1-2):148-60. [PubMed:15522831 ]
  3. Burgermeister M, Birner-Grunberger R, Nebauer R, Daum G: Contribution of different pathways to the supply of phosphatidylethanolamine and phosphatidylcholine to mitochondrial membranes of the yeast Saccharomyces cerevisiae. Biochim Biophys Acta. 2004 Nov 8;1686(1-2):161-8. [PubMed:15522832 ]
  4. Roggero R, Zufferey R, Minca M, Richier E, Calas M, Vial H, Ben Mamoun C: Unraveling the mode of action of the antimalarial choline analog G25 in Plasmodium falciparum and Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2004 Aug;48(8):2816-24. [PubMed:15273086 ]
  5. Voelker DR: Protein and lipid motifs regulate phosphatidylserine traffic in yeast. Biochem Soc Trans. 2005 Nov;33(Pt 5):1141-5. [PubMed:16246067 ]
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. PTDSS2 is specific for phosphatatidylethanolamine and does not act on phosphatidylcholine.
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Molecular weight:
  1. Bergo MO, Gavino BJ, Steenbergen R, Sturbois B, Parlow AF, Sanan DA, Skarnes WC, Vance JE, Young SG: Defining the importance of phosphatidylserine synthase 2 in mice. J Biol Chem. 2002 Dec 6;277(49):47701-8. Epub 2002 Oct 1. [PubMed:12361952 ]
  2. Vance JE, Vance DE: Phospholipid biosynthesis in mammalian cells. Biochem Cell Biol. 2004 Feb;82(1):113-28. [PubMed:15052332 ]
  3. Dygas A, Baranska J, Santella L: Ca2+-dependent phosphatidylserine synthesis in immature and mature starfish oocytes. Acta Biochim Pol. 2003;50(2):377-87. [PubMed:12833164 ]
  4. Grandmaison PA, Nanowski TS, Vance JE: Externalization of phosphatidylserine during apoptosis does not specifically require either isoform of phosphatidylserine synthase. Biochim Biophys Acta. 2004 Feb 27;1636(1):1-11. [PubMed:14984733 ]
  5. Wen Z, Kim HY: Inhibition of phosphatidylserine biosynthesis in developing rat brain by maternal exposure to ethanol. J Neurosci Res. 2007 May 15;85(7):1568-78. [PubMed:17387686 ]
General function:
Involved in metal ion binding
Specific function:
Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:
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  1. Krut O, Wiegmann K, Kashkar H, Yazdanpanah B, Kronke M: Novel tumor necrosis factor-responsive mammalian neutral sphingomyelinase-3 is a C-tail-anchored protein. J Biol Chem. 2006 May 12;281(19):13784-93. Epub 2006 Mar 3. [PubMed:16517606 ]
  2. Marchesini N, Luberto C, Hannun YA: Biochemical properties of mammalian neutral sphingomyelinase 2 and its role in sphingolipid metabolism. J Biol Chem. 2003 Apr 18;278(16):13775-83. Epub 2003 Feb 3. [PubMed:12566438 ]
General function:
Involved in metal ion binding
Specific function:
Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:
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Molecular weight:
  1. Krut O, Wiegmann K, Kashkar H, Yazdanpanah B, Kronke M: Novel tumor necrosis factor-responsive mammalian neutral sphingomyelinase-3 is a C-tail-anchored protein. J Biol Chem. 2006 May 12;281(19):13784-93. Epub 2006 Mar 3. [PubMed:16517606 ]