Structure database (LMSD)

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LM IDLMGP21030003
Common NameAm-PE(P-20:0/20:4(5Z,8Z,11Z,14Z))
Systematic NameN-(1-deoxyfructosyl)-1-(1Z-eicosenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-
glycero-3-phosphoethanolamine
SynonymsAmadori-PE P-20:0/20:4
Exact Mass
941.6357 (neutral)    Calculate m/z:
FormulaC51H92NO12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamine glycans [GP21]
Sub Class1-(1Z-alkenyl),2-acylglycerophosphoethanolamine glycans [GP2103]
AbbrevAm-Hex-PE O-40:5
Abbrev ChainsAm-Hex-PE P-20:0/20:4
PubChem CID-
InChIKeyDQGLIPPKFNXFHB-WEZAJZRTSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C51H92NO12P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-40-60-42-46(43-63-65(58,59)62-41-39-52-45-51(57)50(56)49(55)47(53)44-61-51)64-48(54)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,24,26,30,32,37,40,46-47,49-50,52-53,55-57H,3-11,13,15-17,19,21-23,25,27-29,31,33-36,38-39,41-45H2,1-2H3,(H,58,59)/b14-12-,20-18-,26-24-,32-30-,40-37-/t46-,47-,49-,50+,51-/m1/s1
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SMILES
C1[C@@H](O)[C@@H](O)[C@H](O)[C@@](O)(CNCCOP(OC[C@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO/C=C\CCCCCCCCCCCCCCCCCC)(=O)O)O1
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms65Rings1Aromatic RingsRotatable Bonds45
 van der Waals
Molecular Volume
998.97Topological Polar
Surface Area
195.54Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
13
 logP14.06Molar
Refractivity
266.42    
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.