Structure Database (LMSD)

Common Name
1-(11Z-octadecenoyl)-2-(hexadecenoyl)-sn-glycero-3-phospho-2'-alpha-D-6-glucosaminyl-sn-glycerol
Systematic Name
1-(11Z-octadecenoyl)-2-(hexadecenoyl)-sn-glycero-3-phospho-2'-α-D-6-glucosaminyl-sn-glycerol
Synonyms
LM ID
LMGP14010005
Status
Active
Exact Mass
Calculate m/z
909.594247
Formula


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MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

String Representations

InChiKey (Click to copy)
DHTYGEHOEPWCHB-KKEAVNNNSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[H][C@](O[C@@H]1[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O1)(CO)COP(OC[C@]([H])(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCC/C=C\CCCCCC)=O)(=O)O

References

Reference
Identification 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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Pseudomonas aeruginosa (#287)
Gammaproteobacteria (#1236)
Identification by mass spectrometry of glucosaminylphosphatidylglycerol, a phosphatidylglycerol derivative, produced by Pseudomonas aeruginosa.,
Rapid Commun Mass Spectrom, 2018
Pubmed ID: 30171632

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 62
Rings 1
Aromatic Rings 0
Rotatable Bonds 44
Van der Waals Molecular Volume 937.97
Topological Polar Surface Area 235.83
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 15
logP 11.84
Molar Refractivity 245.92

Admin

Created at
-
Updated at
26th Jul 2021
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.