Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGL02030038
Common Name1-(8-[1]-ladderane-octanyl)-2-(8-[3]-ladderane-octanyl)-sn-glycerol
Systematic Name1-(8-[1]-ladderane-octanyl)-2-(8-[3]-ladderane-octanyl)-sn-glycerol
Synonyms-
Exact Mass
636.5481 (neutral)    Calculate m/z:
FormulaC43H72O3
CategoryGlycerolipids [GL]
Main ClassDiradylglycerols [GL02]
Sub ClassDialkylglycerols [GL0203]
PubChem CID-
InChIKeyKVRRLQJFDRHSFG-CHXUQYPVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H72O3/c44-29-33(30-45-25-13-7-3-1-5-9-15-31-19-21-36-34-17-11-12-18-
35(34)40(36)27-31)46-26-14-8-4-2-6-10-16-32-20-22-39-41(28-32)43-38-24-23-37(38)
42(39)43/h12,18,31-44H,1-11,13-17,19-30H2/t31?,32?,33-,34?,35?,36?,37?,38?,39?,4
0?,41?,42?,43?/m0/s1
SMILESOC[C@@](OCCCCCCCCC1CC2C3C4CCC4C3C2CC1)([H])COCCCCCCCCC1CC2C3C=CCCC3C2CC1
StatusActive
ReferencesStructural identification of ladderane and other membrane lipids of planctomycetes capable of anaerobic ammonium oxidation (anammox)
Jaap S. Sinninghe Damsté, W. Irene C. Rijpstra, Jan A. J. Geenevasen, Marc Strous and Mike S. M Jetten. The FEBS (Federation of European Biochemical Societies) Journal. Volume 272, Issue 16, August 2005, pp. 4270-4283. https://doi.org/10.1111/j.1742-4658.2005.04842.x
https://febs.onlinelibrary.wiley.com/doi/full/10.1111/j.1742-4658.2005.04842.x
Calculated physicochemical properties (?):
 Heavy Atoms46Rings7Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
689.67Topological Polar
Surface Area
38.69Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
3
 logP12.21Molar
Refractivity
191.94    
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.