Structure Database (LMSD)

Common Name
1-O-(2R-methoxy-4Z-heptadecenyl)-sn-glycerol
Systematic Name
1-O-(2R-methoxy-4Z-heptadecenyl)-sn-glycerol
Synonyms
LM ID
LMGL01020048
Status
Active
Exact Mass
Calculate m/z
358.30831
Formula
Abbrev


Download as...
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)
XAKCTRVQNFAAJR-BDNPHABPSA-N
InChi (Click to copy)
InChI=1S/C21H42O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21(24-2)19-25-18-20(23)17-22/h14-15,20-23H,3-13,16-19H2,1-2H3/b15-14-/t20-,21+/m0/s1
SMILES (Click to copy)
[C@](CO)([H])(O)COC[C@H](OC)C/C=C\CCCCCCCCCCCC

References

Reference
Ether lipids. Magnusson Carlos D, Haraldsson Gudmundur G.Chemistry and Physics of Lipids. Volume 164, Issue 5, 2011, pp. 315-340. doi: 10.1016/j.chemphyslip.2011.04.010. Epub 2011 May 8.


https://www.ncbi.nlm.nih.gov/pubmed/21635876

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 19
Van der Waals Molecular Volume 404.38
Topological Polar Surface Area 58.92
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 6.06
Molar Refractivity 107.42

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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.