Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 21:12:04 UTC
Update Date2022-11-30 19:24:49 UTC
HMDB IDHMDB0113055
Secondary Accession NumbersNone
Metabolite Identification
Common NamePE-NMe(16:0/22:4(7Z,10Z,13Z,16Z))
DescriptionPE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) is a monomethylphosphatidylethanolamine. It is a glycerophospholipid, and it 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(16:0/22:4(7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of adrenic acid at the C-2 position. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids are ubiquitous in nature. They are key components of the cell lipid bilayer and are involved in metabolism and signaling.
Structure
Data?1563873324
Synonyms
ValueSource
1-palmitoyl-2-adrenoyl-sn-glycero-3-phosphoethanolamine-N-monomethylSMPDB, HMDB
PE-NMe(16:0/22:4)SMPDB, HMDB
PE-NMe(16:0/22:4n6)SMPDB, HMDB
PE-NMe(16:0/22:4w6)SMPDB, HMDB
PE-NMe(38:4)SMPDB, HMDB
MMPE(16:0/22:4(7Z,10Z,13Z,16Z))SMPDB, HMDB
MMPE(16:0/22:4)SMPDB, HMDB
MMPE(16:0/22:4n6)SMPDB, HMDB
MMPE(16:0/22:4w6)SMPDB, HMDB
MMPE(38:4)SMPDB, HMDB
monomethylphosphatidylethanolamineSMPDB, HMDB
N-monomethylphosphatidylethanolamineSMPDB, HMDB
phosphatidyl-N-methylethanolamineSMPDB, HMDB
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z))SMPDB
{2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-(hexadecanoyloxy)propoxy}[2-(methylamino)ethoxy]phosphinateGenerator, HMDB
Chemical FormulaC44H80NO8P
Average Molecular Weight782.097
Monoisotopic Molecular Weight781.562155538
IUPAC Name{2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-(hexadecanoyloxy)propoxy}[2-(methylamino)ethoxy]phosphinic acid
Traditional Name2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-(hexadecanoyloxy)propoxy(2-(methylamino)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H]C(COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H80NO8P/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45-3)40-50-43(46)36-34-32-30-28-26-24-17-15-13-11-9-7-5-2/h12,14,18-19,21-22,25,27,42,45H,4-11,13,15-17,20,23-24,26,28-41H2,1-3H3,(H,48,49)/b14-12-,19-18-,22-21-,27-25-
InChI KeyQDZHIMAOKLYMBE-PBKISUJMSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
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
logP9ALOGPS
logP11.89ChemAxon
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
Refractivity227.85 m³·mol⁻¹ChemAxon
Polarizability96.29 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]+299.97331661259
DarkChem[M-H]-288.73731661259
DeepCCS[M+H]+261.63630932474
DeepCCS[M-H]-259.31130932474
DeepCCS[M-2H]-292.19430932474
DeepCCS[M+Na]+267.71230932474
AllCCS[M+H]+284.732859911
AllCCS[M+H-H2O]+284.532859911
AllCCS[M+NH4]+284.832859911
AllCCS[M+Na]+284.832859911
AllCCS[M-H]-278.132859911
AllCCS[M+Na-2H]-285.432859911
AllCCS[M+HCOO]-293.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z))[H]C(COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC5153.5Standard polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z))[H]C(COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC4957.3Standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z))[H]C(COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC5400.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O[Si](C)(C)C5405.8Semi standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O[Si](C)(C)C5028.3Standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O[Si](C)(C)C5764.3Standard polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN(C)[Si](C)(C)C5603.3Semi standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN(C)[Si](C)(C)C4876.8Standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN(C)[Si](C)(C)C6432.4Standard polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O[Si](C)(C)C(C)(C)C5625.7Semi standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O[Si](C)(C)C(C)(C)C5042.6Standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O[Si](C)(C)C(C)(C)C5759.3Standard polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN(C)[Si](C)(C)C(C)(C)C5816.2Semi standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN(C)[Si](C)(C)C(C)(C)C4955.3Standard non polar33892256
PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)),1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN(C)[Si](C)(C)C(C)(C)C6375.8Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) 10V, Negative-QTOFsplash10-0f89-1300000900-88e5a10c89f440cc54482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) 20V, Negative-QTOFsplash10-0kcs-6974500300-4f0b815a35da3859a6402021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) 40V, Negative-QTOFsplash10-0fb9-9521000000-bb176e39dde8143e6c492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) 10V, Positive-QTOFsplash10-001i-2100002900-50bed06807baeca1d73e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) 20V, Positive-QTOFsplash10-0a4i-8100009500-768eebfc738aab4ea85c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE-NMe(16:0/22:4(7Z,10Z,13Z,16Z)) 40V, Positive-QTOFsplash10-0a4i-7921000000-4df5f8923684d26db6c52021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131820170
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 ReferencesNot Available