Structure database (LMSD)

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LM IDLMGP02010052
Common NamePE(18:1(9Z)/18:1(9Z))
Systematic Name1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
SynonymsDioleoyl phosphatidylethanolamine; 9-Octadecenoic acid (Z)-, 1-[[[(2-
aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, (R)-; Ethanol,
2-amino-, dihydrogen phosphate (ester), monoester with 1,2-diolein, L-; Olein,
1,2-di-, 2-aminoethyl hydrogen phosphate, L-; 1,2-Dioleoyl-sn-gl; PE(18:1/18:1)
; PE(36:2); PE(18:1_18:1)
Exact Mass
743.5465 (neutral)    Calculate m/z:
FormulaC41H78NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassDiacylglycerophosphoethanolamines [GP0201]
LIPIDAT ID5785
PubChem CID9546757
HMDB IDHMDB0009059
SWISSLIPIDS IDSLM:000034898
CAYMAN ID15091
InChIKeyMWRBNPKJOOWZPW-NYVOMTAGSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C41H78NO8P/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/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/b19-17-,20-18-/t39-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCN)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O
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MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
Ion mobilityView Ion mobility data
MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms51Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
808.45Topological Polar
Surface Area
134.38Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP13.20Molar
Refractivity
212.86    
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.