Structure database (LMSD)

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LM IDLMGP14010005
Common Name1-(11Z-octadecenoyl)-2-(hexadecenoyl)-sn-glycero-3-phospho-2'-α-D-6-
glucosaminyl-sn-glycerol
Systematic Name1-(11Z-octadecenoyl)-2-(hexadecenoyl)-sn-glycero-3-phospho-2'-α-D-6-
glucosaminyl-sn-glycerol
Synonyms-
Exact Mass
909.5942 (neutral)    Calculate m/z:
FormulaC46H88NO14P
CategoryGlycerophospholipids [GP]
Main ClassGlycosylglycerophospholipids [GP14]
Sub ClassDiacylglycosylglycerophospholipids [GP1401]
PubChem CID138454235
InChIKeyDHTYGEHOEPWCHB-IRBSCINHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C46H88NO14P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)56-35-39(59-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)37-58-62(54,55)57-36-38(33-48)60-46-43(47)45(53)44(52)40(34-49)61-46/h13,15,38-40,43-46,48-49,52-53H,3-12,14,16-37,47H2,1-2H3,(H,54,55)/b15-13-/t38-,39+,40+,43?,44+,45?,46-/m0/s1
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SMILES
[H][C@](O[C@H]1O[C@H](CO)[C@@H](O)C(O)C1N)(CO)COP(OC[C@]([H])(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCC/C=C\CCCCCC)=O)(=O)O
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StatusActive
ReferencesIdentification by mass spectrometry of glucosaminylphosphatidylglycerol, a phosphatidylglycerol derivative, produced by Pseudomonas aeruginosa. Imen Abbes, Christophe Rihouey, Julie Hardouin, Thierry Jouenne, Emmanuelle De and Stéphane Alexandre. Rapid Communications in Mass Spectrometry. Volume 32, Issue 24. September 2018. DOI: https://doi.org/10.1002/rcm.8277

https://onlinelibrary.wiley.com/doi/10.1002/rcm.8277
Calculated physicochemical properties (?):
 Heavy Atoms62Rings1Aromatic Rings0Rotatable Bonds44
 van der Waals
Molecular Volume
937.97Topological Polar
Surface Area
235.83Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
15
 logP11.84Molar
Refractivity
245.92    
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.