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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-24 10:46:40 UTC
Update Date2021-09-14 15:00:41 UTC
HMDB IDHMDB0010567
Secondary Accession Numbers
  • HMDB10567
Metabolite Identification
Common NamePE-NMe(16:0/16:0)
DescriptionPE-NMe(16:0/16:0) is a monomethylphosphatidylethanolamine. It is a glycerophospholipid, and is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Monomethylphosphatidylethanolamines are usually found at trace levels in animal or plant tissues. They can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PE-NMe(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.
Structure
Data?1582752845
Synonyms
ValueSource
alpha-Monomethyl dipalmitoylphosphatidylethanolamineMeSH, HMDB
DP(Me)peMeSH, HMDB
Chemical FormulaC38H76NO8P
Average Molecular Weight705.9857
Monoisotopic Molecular Weight705.530854925
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy][2-(methylamino)ethoxy]phosphinic acid
Traditional Name(2R)-2,3-bis(hexadecanoyloxy)propoxy(2-(methylamino)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C38H76NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-37(40)44-34-36(35-46-48(42,43)45-33-32-39-3)47-38(41)31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h36,39H,4-35H2,1-3H3,(H,42,43)/t36-/m1/s1
InChI KeyQSBINWBNXWAVAK-PSXMRANNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monomethylphosphatidylethanolamines. These are lipids with a structure containing a glycerol moiety linked at its terminal C3 atom to a N-methylphosphoethanolamine group, and at its C1 and C2 terminal atoms by an acyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentMonomethylphosphatidylethanolamines
Alternative Parents
Substituents
  • Monomethylphosphatidylethanolamine
  • 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
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.5e-05 g/LALOGPS
logP10(8.49) g/LALOGPS
logP10(10.67) g/LChemAxon
logS10(-7.1) g/LALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)10.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.39 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity195.78 m³·mol⁻¹ChemAxon
Polarizability87.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+273.42631661259
DarkChem[M-H]-263.38231661259

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 19V, positive-QTOFsplash10-0a4i-0000000900-74c2a17ee8a050244ddc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 29V, positive-QTOFsplash10-0pcr-0900040800-bb740f8bad5a5460c3f32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 39V, positive-QTOFsplash10-001i-0900020000-49fdf2cdcd5934eecb862020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 49V, positive-QTOFsplash10-001i-0900010000-ce07173cbdabd0e61e552020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 59V, positive-QTOFsplash10-001i-1900000000-20558dd32e91592401952020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 69V, positive-QTOFsplash10-001i-2900000000-bffb08a2a4b82beaf9fa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 79V, positive-QTOFsplash10-001i-4900000000-3c72adb95f307ff4be812020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 88V, positive-QTOFsplash10-001i-5900000000-cd5c9357aa87d362401d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 98V, positive-QTOFsplash10-001r-6900000000-ee4e2718fe9bacbf04722020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 118V, positive-QTOFsplash10-0080-9800000000-5a547a7b9809b548df522020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 148V, positive-QTOFsplash10-00dr-9500000000-8506b810ea7e725831672020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 179V, positive-QTOFsplash10-00ds-9300000000-25c7b2e63cfd7905315c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 218V, positive-QTOFsplash10-006t-9100000000-ae107bb2588527e601432020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 258V, positive-QTOFsplash10-0002-9000000000-840e349154b0295fc31a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) Orbitrap 318V, positive-QTOFsplash10-0002-9000000000-2feda801a4c3a24157082020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) n/a 49V, positive-QTOFsplash10-0udi-0000090000-6930912891e0cd057b6f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) n/a 49V, positive-QTOFsplash10-000i-0090000000-65ff9dc5edb4eeddcda12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) n/a 49V, positive-QTOFsplash10-0udi-0003900000-178054f64762dc8354cc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - PE-NMe(16:0/16:0) n/a 49V, positive-QTOFsplash10-004i-0009000000-6f902c70c19ad125df4b2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/16:0) 10V, Negative-QTOFsplash10-0udi-0200002900-adf715e3083e3f27c0c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/16:0) 20V, Negative-QTOFsplash10-0udi-6971611400-26749e0749105a9236c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/16:0) 40V, Negative-QTOFsplash10-0fb9-9630000000-5955ed9f8814d401e6672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/16:0) 10V, Positive-QTOFsplash10-0a4i-3100022900-9369004f3acb044a439a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/16:0) 20V, Positive-QTOFsplash10-0a4i-9200053000-e40d1ce4f547db7c4c4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/16:0) 40V, Positive-QTOFsplash10-0a4i-6920000000-4ddeb632bd677fafbe4f2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027717
KNApSAcK IDNot Available
Chemspider ID7825981
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547031
PDB IDNot Available
ChEBI IDNot Available
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  8. 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..