Structure Database (LMSD)

Common Name
Ricinolein
Systematic Name
1,2,3-tri-(12R-hydroxy-9Z-octadecenoyl)-sn-glycerol
Synonyms
  • 1,2,3-triricinoleyoyl-glycerol
  • Glyceryl triricinoleate
LM ID
LMGL03016900
Status
Active
Exact Mass
Calculate m/z
932.768035
Formula
Abbrev
Abbrev Chains
TG 18:1;O_18:1;O_18:1:O


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)
ZEMPKEQAKRGZGQ-VBJOUPRGSA-N
InChi (Click to copy)
InChI=1S/C57H104O9/c1-4-7-10-31-40-51(58)43-34-25-19-13-16-22-28-37-46-55(61)64-49-54(66-57(63)48-39-30-24-18-15-21-27-36-45-53(60)42-33-12-9-6-3)50-65-56(62)47-38-29-23-17-14-20-26-35-44-52(59)41-32-11-8-5-2/h25-27,34-36,51-54,58-60H,4-24,28-33,37-50H2,1-3H3/b34-25-,35-26-,36-27-/t51-,52-,53-/m1/s1
SMILES (Click to copy)
C(OC(=O)CCCCCCC/C=C\C[C@H](O)CCCCCC)[C@]([H])(OC(CCCCCCC/C=C\C[C@H](O)CCCCCC)=O)COC(CCCCCCC/C=C\C[C@H](O)CCCCCC)=O

References

Reference
The fatty acids and glycerides of castor oil
J Sci Food Agric. 1951
10.1002/jsfa.2740020603

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ricinus communis (#3988)
Magnoliopsida (#3398)
The fatty acids and glycerides of castor oil,
J Sci Food Agric., 1951

Other Databases

Wikipedia
CHEBI ID
PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 66
Rings 0
Aromatic Rings 0
Rotatable Bonds 53
Van der Waals Molecular Volume 1057.93
Topological Polar Surface Area 139.59
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 9
logP 16.72
Molar Refractivity 277.35

Admin

Created at
4th May 2021
Updated at
13th May 2021
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.