Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGL01010036
Common NameSciadonoyl-2-glycerol
Systematic Name2-(5Z,11Z,14Z-eicosatrienoyl)-sn-glycerol
Synonyms2-SG
Exact Mass
380.2927 (neutral)    Calculate m/z:
FormulaC23H40O4
CategoryGlycerolipids [GL]
Main ClassMonoradylglycerols [GL01]
Sub ClassMonoacylglycerols [GL0101]
AbbrevMG 20:3
PubChem CID101046553
InChIKeyKXAFDKQQSSWDNZ-URZBRJKDSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C23H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,15-16,22,24-25H,2-5,8,11-14,17-21H2,1H3/b7-6-,10-9-,16-15-
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SMILES
OC[C@]([H])(OC(CCC/C=C\CCCC/C=C\C/C=C\CCCCC)=O)CO
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StatusActive
ReferencesNovel CB1-ligands maintain homeostasis of the endocannabinoid system in w3 and w6 long-chain-PUFA deficiency
Ina Hammels, Erika Binczek, Inga Schmidt-Soltau, Britta Jenke, Andreas Thomas, Matthias Vogel, Mario Thevis, Dilyana Filipova, Symeon Papadopoulos and Wilhelm Stoffel. J. Lipid Res., 60, 1396-1409 (2019). doi: 10.1194/jlr.M094664
Calculated physicochemical properties (?):
 Heavy Atoms27Rings0Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
431.06Topological Polar
Surface Area
66.76Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
4
 logP6.11Molar
Refractivity
114.04    
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.