Structure Database (LMSD)

Common Name
Topsentolide A2
Systematic Name
11R,12S-epoxy-5Z,9E,14Z-eicosatrien-8R-olide
Synonyms
LM ID
LMFA07040133
Formula
C20H30O3
Exact Mass
Calculate m/z
318.219495
Sum Composition
FA 20:5;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Lactones [FA0704]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
unclassified Topsentia (#2622176)
Demospongiae (#6042)
Cytotoxic oxylipins from a marine sponge Topsentia sp.,
J Nat Prod, 2006
Pubmed ID: 16643027
unclassified Topsentia (#2622176)
Demospongiae (#6042)
Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter,
Tetrahedron, 2014

String Representations

InChiKey (Click to copy)
MWTCCFSVIGUOIH-NGSXCRDOSA-N
InChi (Click to copy)
InChI=1S/C20H30O3/c1-2-3-4-5-6-10-13-18-19(23-18)16-15-17-12-9-7-8-11-14-20(21)22-17/h6-7,9-10,15-19H,2-5,8,11-14H2,1H3/b9-7-,10-6-,16-15+/t17-,18+,19-/m1/s1
SMILES (Click to copy)
C(/[C@@H]1OC(=O)CCCC=CC1)=C\[C@@]1([H])O[C@@]1([H])C/C=C\CCCCC

Other Databases

PubChem CID
77846324

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 2
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 345.65
Topological Polar Surface Area 40.90
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 3
logP 5.74
Molar Refractivity 94.72

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Created at
28th Sep 2020
Updated at
28th Sep 2020