LIPID MAPS

Structure Database (LMSD)

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Common Name

Gliomasolide B

Systematic Name

8R-(α-D-glucopyranosyl)-4S,5S-dihydroxy-2E-octadecen-13R-olide

Synonyms

(3E,5R,6S,8R,14R)-5,6-dihydroxy-14-pentyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-oxacyclotetradec-3-en-2-one

LM ID

LMFA07040203

Formula

C₂₄H₄₂O₁₀

Exact Mass

Calculate m/z

490.277801

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

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

DOI: 10.1039/C5RA08559D

String Representations

InChiKey (Click to copy)

JRUPWHSLHIDIPV-RHDNBBMPSA-N

InChi (Click to copy)

InChI=1S/C24H42O10/c1-2-3-5-8-15-9-6-4-7-10-16(13-18(27)17(26)11-12-20(28)32-15)33-24-23(31)22(30)21(29)19(14-25)34-24/h11-12,15-19,21-27,29-31H,2-10,13-14H2,1H3/b12-11+/t15-,16-,17-,18+,19-,21-,22+,23-,24+/m1/s1

SMILES (Click to copy)

C1(C=C[C@@H](O)[C@@H](O)C[C@H](O[C@@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CCCCC[C@H](O1)CCCCC)=O

Other Databases

PubChem CID

139200423

Calculated Physicochemical Properties

Heavy Atoms 34

Rings 2

Aromatic Rings

Rotatable Bonds 7

Van der Waals Molecular Volume 481.66

Topological Polar Surface Area 170.28

Hydrogen Bond Donors 6

Hydrogen Bond Acceptors 10

logP 3.16

Molar Refractivity 126.62

Admin

Created at

21st Jan 2025

Updated at