Structure Database (LMSD)

Common Name
Topsentolide C1
Systematic Name
11S-methoxy,12S-hydroxy-5Z,9E,14Z,17Z-eicosatetraen-8R-olide
Synonyms
LM ID
LMFA07040135
Formula
C21H32O4
Exact Mass
Calculate m/z
348.23006
Sum Composition
FA 21:5;O2
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)
QXHLHGKKWDCOOY-ARTHJQAWSA-N
InChi (Click to copy)
InChI=1S/C21H32O4/c1-3-4-5-6-7-11-14-19(22)20(24-2)17-16-18-13-10-8-9-12-15-21(23)25-18/h4-5,7-8,10-11,16-20,22H,3,6,9,12-15H2,1-2H3/b5-4-,10-8-,11-7-,17-16+/t18-,19+,20+/m1/s1
SMILES (Click to copy)
C(/[C@@H]1OC(=O)CCCC=CC1)=C\[C@H](OC)[C@H](C/C=C\C/C=C\CC)O

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 381.46
Topological Polar Surface Area 57.83
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 5.12
Molar Refractivity 102.77

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