Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGL05010041
Common NameLinolipin D
Systematic Name1,2-di-(12-(1'Z,3'Z-hexadienyloxy)-9Z,11E-dodecadienoyl)-3-O-(α-D-galactosyl1-
6)-β-D-galactosyl-sn-glycerol
Synonyms1,2-di-O-(ω5Z)-etherolenoyl-3-O-(α-D-galactosyl1-6)-β-D-galactosyl-sn-
glycerol; DGDG(18:4;O/18:4;O)
Exact Mass
964.5396 (neutral)    Calculate m/z:
FormulaC51H80O17
CategoryGlycerolipids [GL]
Main ClassGlycosyldiradylglycerols [GL05]
Sub ClassGlycosyldiacylglycerols [GL0501]
AbbrevDGDG 36:8;O2
Abbrev ChainsDGDG 18:4;O/18:4;O
PubChem CID102583563
InChIKeySBOCFWSPOCJDHY-QENYLQOYSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C51H80O17/c1-3-5-7-25-31-61-33-27-21-17-13-9-11-15-19-23-29-42(53)63-36-39(66-43(54)30-24-20-16-12-10-14-18-22-28-34-62-32-26-8-6-4-2)37-64-50-49(60)47(58)45(56)41(68-50)38-65-51-48(59)46(57)44(55)40(35-52)67-51/h5-8,17-18,21-22,25-28,31-34,39-41,44-52,55-60H,3-4,9-16,19-20,23-24,29-30,35-38H2,1-2H3/b7-5-,8-6-,21-17-,22-18-,31-25-,32-26-,33-27+,34-28+/t39-,40-,41-,44+,45+,46+,47+,48-,49-,50-,51+/m1/s1
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SMILES
O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO[C@@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)O1)C[C@]([H])(OC(CCCCCCC/C=C\C=C\O/C=C\C=C/CC)=O)COC(CCCCCCC/C=C\C=C\O/C=C\C=C/CC)=O
Click to highlight SMILES
StatusActive
ReferencesIsolation and structure elucidation of linolipins C and D, complex oxylipins from flax leaves
Phytochemistry 2013
DOI: 10.1016/j.phytochem.2013.08.010
PMID: 24042063
Calculated physicochemical properties (?):
 Heavy Atoms68Rings2Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
989.17Topological Polar
Surface Area
253.73Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
17
 logP9.97Molar
Refractivity
261.29    
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.