Structure Database (LMSD)

Common Name
Gliomasolide E
Systematic Name
5R,7R,9R-trihydroxy-2E-octadecen-13R-olide
Synonyms
  • (3E,6R,8R,10R,14R)-6,8,10-trihydroxy-14-pentyl-1-oxacyclotetradec-3-en-2-one
LM ID
LMFA07040206
Formula
C18H32O5
Exact Mass
Calculate m/z
328.224976
Sum Composition
FA 18:2;O3
Status
Curated
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
Gliomastix sp. ZSDS1-F7-2 (#1777006)
Sordariomycetes (#147550)
Gliomasolides A–E, unusual macrolides from a sponge-derived fungus Gliomastix sp. ZSDS1-F7-2,
RSC Adv, 2015
Gliomastix sp. ZSDS1-F7-2 (#1777006)
Sordariomycetes (#147550)
Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide E and Its Structural Elucidation.,
J Org Chem, 2017
Pubmed ID: 27992722

String Representations

InChiKey (Click to copy)
CIKXQDGRSUPQKJ-IGSZESLRSA-N
InChi (Click to copy)
InChI=1S/C18H32O5/c1-2-3-4-9-17-10-5-7-14(19)12-16(21)13-15(20)8-6-11-18(22)23-17/h6,11,14-17,19-21H,2-5,7-10,12-13H2,1H3/b11-6+/t14-,15-,16-,17-/m1/s1
SMILES (Click to copy)
C1(C=CC[C@@H](O)C[C@H](O)C[C@H](O)CCC[C@H](O1)CCCCC)=O

Other Databases

PubChem CID
132961946

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings
Rotatable Bonds 4
Van der Waals Molecular Volume 346.27
Topological Polar Surface Area 89.06
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.62
Molar Refractivity 90.93

Admin

Created at
21st Jan 2025
Updated at
21st Jan 2025