Structure Database (LMSD)

Common Name
Arabidopside B
Systematic Name
1,2-di((1S,2S)-3-oxo-2-(2'Z-pentenyl)cyclopent-4-eneoctanoyl)-3-O-β-D-galactosyl-sn-glycerol
Synonyms
  • MGDG(di-12-oxo-PDA)
  • MGDG(di-12-oxo-phytodienoic acid)
LM ID
LMGL05010034
Status
Active
Exact Mass
Calculate m/z
802.48673
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)
SYJOSMLJXIQXFJ-YENLXDNHSA-N
InChi (Click to copy)
InChI=1S/C45H70O12/c1-3-5-13-21-35-32(25-27-37(35)47)19-15-9-7-11-17-23-40(49)54-30-34(31-55-45-44(53)43(52)42(51)39(29-46)57-45)56-41(50)24-18-12-8-10-16-20-33-26-28-38(48)36(33)22-14-6-4-2/h5-6,13-14,25-28,32-36,39,42-46,51-53H,3-4,7-12,15-24,29-31H2,1-2H3/b13-5-,14-6-/t32-,33-,34+,35-,36-,39+,42-,43-,44+,45+/m0/s1
SMILES (Click to copy)
C(O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)[C@]([H])(OC(=O)CCCCCCC[C@H]1C=CC(=O)[C@H]1C/C=C\CC)COC(=O)CCCCCCC[C@H]1C=CC(=O)[C@H]1C/C=C\CC

References

Reference
Arabidopsides A and B, two new oxylipins from Arabidopsis thaliana
Tetrahedron Letters 2003
DOI: 10.1016/S0040-4039(03)01148-1

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Arabidopsis thaliana (#3702)
Magnoliopsida (#3398)
Arabidopsides A and B, two new oxylipins from Arabidopsis thaliana,
Tetrahedron Lett, 2003

Calculated Physicochemical Properties

Heavy Atoms 57
Rings 3
Aromatic Rings 0
Rotatable Bonds 31
Van der Waals Molecular Volume 834.34
Topological Polar Surface Area 188.19
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 12
logP 8.75
Molar Refractivity 220.09

Admin

Created at
29th Jul 2020
Updated at
29th Jul 2020
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.