Structure database (LMSD)

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LM IDLMGP21030008
Common NameAm-PE(P-18:0/18:2(9Z,12Z))
Systematic NameN-(1-deoxyfructosyl)-1-(1Z-octadecenyl)-2-(9Z,12Z-octadecadienoyl)-glycero-3-
phosphoethanolamine
SynonymsAmadori-PE P-18:0/18:2
Exact Mass
889.6044 (neutral)    Calculate m/z:
FormulaC47H88NO12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamine glycans [GP21]
Sub Class1-(1Z-alkenyl),2-acylglycerophosphoethanolamine glycans [GP2103]
AbbrevAm-Hex-PE O-36:3
Abbrev ChainsAm-Hex-PE P-18:0/18:2
PubChem CID-
InChIKeyJPIWFWWTVWFSMH-OWOVGBLNSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C47H88NO12P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-36-56-38-42(60-44(50)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)39-59-61(54,55)58-37-35-48-41-47(53)46(52)45(51)43(49)40-57-47/h12,14,18,20,33,36,42-43,45-46,48-49,51-53H,3-11,13,15-17,19,21-32,34-35,37-41H2,1-2H3,(H,54,55)/b14-12-,20-18-,36-33-/t42-,43-,45-,46+,47-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCNC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O)([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)CO/C=C\CCCCCCCCCCCCCCCC
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms61Rings1Aromatic RingsRotatable Bonds43
 van der Waals
Molecular Volume
935.05Topological Polar
Surface Area
195.54Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
13
 logP12.95Molar
Refractivity
248.14    
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.