Structure Database (LMSD)

Common Name
Peyssonenyne B
Systematic Name
2-(8Z,12Z,15Z-8-acetyloxyoctadecatrien-4,6-diynoyl)-glycerol
Synonyms
LM ID
LMGL01010042
Formula
C23H30O6
Exact Mass
Calculate m/z
402.204241
Sum Composition
MG 20:8;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Glycerolipids [GL]
Monoradylglycerols [GL01]
Monoacylglycerols [GL0101]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sonderophycus cauliferus (#339600)
Florideophyceae (#2806)
Peyssonenynes a and B, novel enediyne oxylipins with DNA methyl transferase inhibitory activity from the red marine alga peyssonneliacaulifera.,
J Nat Prod, 2004
Pubmed ID: 15217284
Sonderophycus cauliferus (#339600)
Florideophyceae (#2806)
Total synthesis of the proposed structures of the DNA methyl transferase inhibitors peyssonenynes, and structural revision of peyssonenyne B.,
Org Biomol Chem, 2011
Pubmed ID: 21858378

String Representations

InChiKey (Click to copy)
RVSNTLVXJQULRJ-XUKRHBIOSA-N
InChi (Click to copy)
InChI=1S/C23H30O6/c1-3-4-5-6-7-8-9-12-15-21(28-20(2)26)16-13-10-11-14-17-23(27)29-22(18-24)19-25/h4-5,7-8,15,22,24-25H,3,6,9,12,14,17-19H2,1-2H3/b5-4-,8-7-,21-15-
SMILES (Click to copy)
C(CCC#CC#C/C(/OC(=O)C)=C/CC/C=C\C/C=C\CC)(=O)OC(CO)CO

Other Databases

PubChem CID
54577195

Calculated Physicochemical Properties

Heavy Atoms 29
Rings
Aromatic Rings
Rotatable Bonds 14
Van der Waals Molecular Volume 435.44
Topological Polar Surface Area 93.06
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 6
logP 3.67
Molar Refractivity 112.60

Admin

Created at
17th Apr 2026
Updated at
17th Apr 2026
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.