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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-05-17 01:25:22 UTC
Update Date2021-09-14 15:42:34 UTC
HMDB IDHMDB0060501
Secondary Accession Numbers
  • HMDB60501
Metabolite Identification
Common NamePhosphatidylethanolamine
DescriptionPhosphatidylethanolamine (cephalin, sometimes abbreviated PE) is a lipid found in biological membranes. It is synthesized by the addition of CDP-ethanolamine to diglyceride, releasing CMP. S-adenosyl methionine can subsequently methylate the amine of phosphatidyl ethanolamine to yield phosphatidyl choline. Cephalin is a phospholipid, which is a lipid derivative. It is not to be confused with the molecule of the same name that is an alkaloid constituent of Ipecac. (Wikipedia )
Structure
Data?1563866068
SynonymsNot Available
Chemical FormulaC41H82NO8P
Average Molecular Weight748.0654
Monoisotopic Molecular Weight747.577805117
IUPAC Name(2-aminoethoxy)[(2S)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2S)-2,3-bis(octadecanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C41H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m0/s1
InChI KeyLVNGJLRDBYCPGB-KDXMTYKHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.4e-05 g/LALOGPS
logP10(8.91) g/LALOGPS
logP10(12.23) g/LChemAxon
logS10(-7.1) g/LALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity209.41 m³·mol⁻¹ChemAxon
Polarizability94.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+284.84331661259
DarkChem[M-H]-270.33631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phosphatidylethanolamine,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5209.8Semi standard non polar33892256
Phosphatidylethanolamine,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4743.7Standard non polar33892256
Phosphatidylethanolamine,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC7265.5Standard polar33892256
Phosphatidylethanolamine,1TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5258.3Semi standard non polar33892256
Phosphatidylethanolamine,1TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4924.1Standard non polar33892256
Phosphatidylethanolamine,1TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC7001.3Standard polar33892256
Phosphatidylethanolamine,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5225.6Semi standard non polar33892256
Phosphatidylethanolamine,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4856.7Standard non polar33892256
Phosphatidylethanolamine,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5890.6Standard polar33892256
Phosphatidylethanolamine,2TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5585.8Semi standard non polar33892256
Phosphatidylethanolamine,2TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4896.4Standard non polar33892256
Phosphatidylethanolamine,2TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC6566.7Standard polar33892256
Phosphatidylethanolamine,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5559.3Semi standard non polar33892256
Phosphatidylethanolamine,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4813.0Standard non polar33892256
Phosphatidylethanolamine,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC7187.9Standard polar33892256
Phosphatidylethanolamine,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5558.1Semi standard non polar33892256
Phosphatidylethanolamine,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC5009.7Standard non polar33892256
Phosphatidylethanolamine,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@@](=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC6835.4Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 10V, Negative-QTOFsplash10-0002-0010000900-60329d5a7c12551bbc422017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 20V, Negative-QTOFsplash10-0002-0010000900-60329d5a7c12551bbc422017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 40V, Negative-QTOFsplash10-001j-0390300600-067b245407347d1176692017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 10V, Positive-QTOFsplash10-0002-0000001900-4a7b6d9013d36f909f902017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 20V, Positive-QTOFsplash10-0a4j-0001309700-eeada937f3ad0f7968a82017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 40V, Positive-QTOFsplash10-0a4i-0001309300-f72f58cbd9cb16b1f4d22017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 10V, Positive-QTOFsplash10-0002-0000001900-bbbbfd5d071fd445575f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 20V, Positive-QTOFsplash10-0a4j-0001309700-96819fbf9850a4df1ffe2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 40V, Positive-QTOFsplash10-0a4i-0001309300-60566be72def6d31ad0d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 10V, Positive-QTOFsplash10-00di-0000001900-50a418c4f44c815f62892021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 20V, Positive-QTOFsplash10-00fr-0000001900-34619ad7f9118f8f30382021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 40V, Positive-QTOFsplash10-004i-0100101900-6718aff73f7bb076a5582021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 10V, Negative-QTOFsplash10-0002-0010000900-6bd6d72f410de62ad7002021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 20V, Negative-QTOFsplash10-0002-0010000900-6bd6d72f410de62ad7002021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylethanolamine 40V, Negative-QTOFsplash10-001j-0390300600-96208b51ba43ac55e6842021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothSchizophrenia details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Kaddurah-Daouk R, McEvoy J, Baillie RA, Lee D, Yao JK, Doraiswamy PM, Krishnan KR: Metabolomic mapping of atypical antipsychotic effects in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):934-45. Epub 2007 Apr 17. [PubMed:17440431 ]
Associated OMIM IDs
DrugBank IDDB01966
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhosphatidylethanolamine
METLIN IDNot Available
PubChem Compound17754131
PDB IDNot Available
ChEBI ID47767
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  9. 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..

Enzymes

General function:
Involved in N-methyltransferase activity
Specific function:
Catalyzes three sequential methylation reactions of phosphatidylethanolamine (PE) by AdoMet, thereby producing phosphatidylcholine (PC).
Gene Name:
PEMT
Uniprot ID:
Q9UBM1
Molecular weight:
23697.395
Reactions
S-Adenosylmethionine + Phosphatidylethanolamine → S-Adenosylhomocysteine + phosphatidyl-N-methylethanolaminedetails
General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Not Available
Gene Name:
PISD
Uniprot ID:
Q9UG56
Molecular weight:
43046.33
Reactions
Phosphatidyl-L-serine → Phosphatidylethanolamine + CO(2)details