Structure Database (LMSD)

Common Name
MGDG-bis-9-OH-traumatin
Systematic Name
1,2-di-(9-hydroxy-12-oxo-10E-dodecenoyl)-3-O-β-D-galactosyl-sn-glycerol
Synonyms
LM ID
LMGL05010033
Status
Active
Exact Mass
Calculate m/z
674.35136
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)
LGAPPEPKENDRBM-DYXOSTSTSA-N
InChi (Click to copy)
InChI=1S/C33H54O14/c34-19-11-15-24(37)13-7-3-1-5-9-17-28(39)44-22-26(23-45-33-32(43)31(42)30(41)27(21-36)47-33)46-29(40)18-10-6-2-4-8-14-25(38)16-12-20-35/h11-12,15-16,19-20,24-27,30-33,36-38,41-43H,1-10,13-14,17-18,21-23H2/b15-11+,16-12+/t24?,25?,26-,27-,30+,31+,32-,33-/m1/s1
SMILES (Click to copy)
O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)C[C@]([H])(OC(CCCCCCCC(O)/C=C/C(=O)[H])=O)COC(CCCCCCCC(O)/C=C/C(=O)[H])=O

References

Reference
Traumatin- and dinortraumatin-containing galactolipids in Arabidopsis: their formation in tissue-disrupted leaves as counterparts of green leaf volatiles
J Biol Chem. 2013
DOI: 10.1074/jbc.M113.487959
PMID: 23888054

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Arabidopsis thaliana (#3702)
Magnoliopsida (#3398)
Traumatin- and dinortraumatin-containing galactolipids in Arabidopsis: their formation in tissue-disrupted leaves as counterparts of green leaf volatiles.,
J Biol Chem, 2013
Pubmed ID: 23888054

Calculated Physicochemical Properties

Heavy Atoms 47
Rings 1
Aromatic Rings 0
Rotatable Bonds 29
Van der Waals Molecular Volume 674.32
Topological Polar Surface Area 228.65
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 14
logP 4.10
Molar Refractivity 173.18

Admin

Created at
28th Jul 2020
Updated at
28th 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.