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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-24 10:42:35 UTC
Update Date2022-11-30 19:03:54 UTC
HMDB IDHMDB0010565
Secondary Accession Numbers
  • HMDB10565
Metabolite Identification
Common NamePE-NMe(18:1(9Z)/18:1(9Z))
DescriptionPE-NMe(18:1(9Z)/18:1(9Z)) 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(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl 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
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-methylethanolamineChEBI
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-methylethanolamine zwitterionChEBI
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine-N-methylChEBI
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine-N-monomethylHMDB
MMPE(18:1(9Z)/18:1(9Z))HMDB
1,2-DOPE-meHMDB
N-Methyl-1,2-dioleoylphosphatidylethanolamineHMDB
N-Methyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamineHMDB
Chemical FormulaC42H80NO8P
Average Molecular Weight758.0603
Monoisotopic Molecular Weight757.562155053
IUPAC Name[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][2-(methylamino)ethoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy(2-(methylamino)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H80NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43-3)51-42(45)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h18-21,40,43H,4-17,22-39H2,1-3H3,(H,46,47)/b20-18-,21-19-/t40-/m1/s1
InChI KeyLPXFOQGBESUDAX-NLEYBKGJSA-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
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
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 Solubility4.1e-05 g/LALOGPS
logP8.95ALOGPS
logP11.73ChemAxon
logS-7.3ALOGPS
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 Count42ChemAxon
Refractivity216.42 m³·mol⁻¹ChemAxon
Polarizability92.11 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]+287.82931661259
DarkChem[M-H]-270.90131661259
DeepCCS[M+H]+285.53230932474
DeepCCS[M-H]-283.13730932474
DeepCCS[M-2H]-316.02130932474
DeepCCS[M+Na]+291.73230932474
AllCCS[M+H]+284.632859911
AllCCS[M+H-H2O]+284.532859911
AllCCS[M+NH4]+284.632859911
AllCCS[M+Na]+284.632859911
AllCCS[M-H]-271.232859911
AllCCS[M+Na-2H]-277.932859911
AllCCS[M+HCOO]-285.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PE-NMe(18:1(9Z)/18:1(9Z))[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCC4762.4Standard polar33892256
PE-NMe(18:1(9Z)/18:1(9Z))[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCC4763.7Standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z))[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCC5215.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PE-NMe(18:1(9Z)/18:1(9Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCNC)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC5159.5Semi standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCNC)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC4942.4Standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCNC)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC5608.1Standard polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN(C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC5432.7Semi standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN(C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC4735.5Standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN(C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC6433.1Standard polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCNC)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC5405.9Semi standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCNC)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC4963.7Standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCCNC)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC5632.5Standard polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN(C)[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC5645.2Semi standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN(C)[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC4790.3Standard non polar33892256
PE-NMe(18:1(9Z)/18:1(9Z)),1TBDMS,isomer #2CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN(C)[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC6368.2Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(18:1(9Z)/18:1(9Z)) 10V, Positive-QTOFsplash10-0a4i-4100005900-24e92de493bfebdc29af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(18:1(9Z)/18:1(9Z)) 20V, Positive-QTOFsplash10-0a4i-9200027200-b26298cbf5753a3524bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(18:1(9Z)/18:1(9Z)) 40V, Positive-QTOFsplash10-0a4i-5910000000-820cfdf69166f9b6c5942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(18:1(9Z)/18:1(9Z)) 10V, Negative-QTOFsplash10-0pb9-1400001900-1bf2d0cd056b3c06f4482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(18:1(9Z)/18:1(9Z)) 20V, Negative-QTOFsplash10-0kdi-5943710300-0421c4df034a85c405272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(18:1(9Z)/18:1(9Z)) 40V, Negative-QTOFsplash10-0fb9-9730100000-9687bb219258fda4d1ab2021-09-23Wishart 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 IDFDB027715
KNApSAcK IDNot Available
Chemspider ID7825982
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547032
PDB IDNot Available
ChEBI ID85679
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..