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Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGL00000135
Common NameDGCC(22:6/20:5)
Systematic Name1-(4Z,7Z,10Z,13Z,16Z,19Z-eicosahexaenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentenoyl)
-sn-glycero-3-O-carboxy- (hydroxymethyl)-choline
Synonyms1-(4Z,7Z,10Z,13Z,16Z,19Z-eicosahexaenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentenoyl)
-sn-glycero-3-O-carboxy- (hydroxymethyl)-choline
Exact Mass
845.5806 (neutral)    Calculate m/z:
FormulaC52H79NO8
CategoryGlycerolipids [GL]
Main ClassOther Glycerolipids [GL00]
Sub Class-
PubChem CID-
InChIKeyXXBDLVNHBQWURH-JDUVWZOCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C52H79NO8/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(54)59-46-48(47-60-52(51(56)57)58-45-44-53(3,4)5)61-50(55)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,25,27,29-32,35-38,48,52H,6-7,12-13,18-19,24,26,28,33-34,39-47H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,27-25-,31-29-,32-30-,37-35-,38-36-/t48-,52?/m1/s1
Click to highlight InChI
SMILES
O(C(C([O-])=O)OCC[N+](C)(C)C)C[C@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
Click to highlight SMILES
StatusActive
ReferencesLipidomics of Thalassiosira pseudonana under Phosphorus Stress Reveal Underlying Phospholipid Substitution Dynamics and Novel Diglycosylceramide Substitutes. Jonathan E. Hunter, Joost Brandsma, Marcus K. Dymond, Grielof Koster, C. Mark Moore, Anthony D. Postle, Rachel A. Mills and George S. Attard. Applied and Environmental Microbiology. Volume 84, Issue 6, pp. 1-17.

https://aem.asm.org/content/aem/84/6/e02034-17.full.pdf
Calculated physicochemical properties (?):
 Heavy Atoms61Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
952.52Topological Polar
Surface Area
111.19Hydrogen
Bond Donors
0Hydrogen
Bond Acceptors
9
 logP12.37Molar
Refractivity
253.87    
LIPID MAPS® abbreviations for glycerolipids (GL)

The LIPID MAPS® glycerolipid abbreviations (MG,DG,TG) are used here to refer to species with one, two or three radyl side-chains, respectively, where the structures of the side chains are indicated within parentheses in the 'Prefix(sn1/sn2/sn3)' format (e.g. TG(16:0/18:1(9Z)/18:0). Acyl chains are assumed by default. The alkyl ether linkage is represented by the 'O-' prefix, e.g. DG(O-16:0/18:1(9Z)/0:0), whereas the 1Z-alkenyl ether (Plasmalogen) linkage is represented by the 'P-' prefix, e.g. and DG(P-14:0/18:1(9Z)/0:0).

For Diradylglycerols and Triradylglycerols, it is not always possible to experimentally determine the exact position of radyl groups on the glycerol group. For Diradylglycerols with two different radyl groups, two different structural isomers exist. For Triradylglycerols with three different radyl groups, six different isomers exist.

Instead of drawing all possible structural isomers explicitly for Diradylglycerols and Triradylglycerols, the LIPID MAPS® abbreviation scheme supports the isomeric specification. A suffix containing 'iso' along with the number of possible isomers is appended to the abbreviation (e.g. [iso2],[iso6]) and a single unique LM_ID is assigned. The structure assigned to the LM_ID corresponds to the radyl substitution shown in the abbreviation. An option is provided to display the other isomers in the group.

The [rac] designation refers to racemic mixtures due to substitution at the sn1 and sn3 positions of glycerol.