Structure Database (LMSD)

Common Name
bhos#26
Systematic Name
3R-hydroxy-15-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-pentadecanoic acid
Synonyms
  • 3R-hydroxy-15-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acid
LM ID
LMFA13040076
Formula
C21H40O7
Exact Mass
Calculate m/z
404.277405
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty acyl glycosides [FA13]
Ascarosides [FA1304]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Caenorhabditis elegans (#6239)
Chromadorea (#119089)
Comparative Metabolomics Reveals Biogenesis of Ascarosides, a Modular Library of Small-Molecule Signals in C. elegans,
J Am Chem Soc, 2012
Pubmed ID: 22239548

String Representations

InChiKey (Click to copy)
CQOIGQHIJMHXGX-HMPZBHLVSA-N
InChi (Click to copy)
InChI=1S/C21H40O7/c1-16-18(23)15-19(24)21(28-16)27-13-11-9-7-5-3-2-4-6-8-10-12-17(22)14-20(25)26/h16-19,21-24H,2-15H2,1H3,(H,25,26)/t16-,17+,18+,19+,21+/m0/s1
SMILES (Click to copy)
O[C@@H]1C[C@@H](O)[C@H](C)O[C@H]1OCCCCCCCCCCCC[C@@H](O)CC(=O)O

Other Databases

CHEBI ID
79263
PubChem CID
86289851
SMID ID
bhos#26

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 418.39
Topological Polar Surface Area 118.52
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 7
logP 4.70
Molar Refractivity 109.01

Admin

Created at
13th Jun 2020
Updated at
13th Jun 2020