Structure Database (LMSD)

Common Name
bhas#40
Systematic Name
3R-hydroxy-21R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-docosanoic acid
Synonyms
  • 3R-hydroxy-21R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-docosanoic acid
LM ID
LMFA13040041
Formula
C28H54O7
Exact Mass
Calculate m/z
502.386955
Status
Curated
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)
KNOOLMWLZZIQFQ-CWEZWLNASA-N
InChi (Click to copy)
InChI=1S/C28H54O7/c1-22(34-28-26(31)21-25(30)23(2)35-28)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-24(29)20-27(32)33/h22-26,28-31H,3-21H2,1-2H3,(H,32,33)/t22-,23+,24-,25-,26-,28-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCCCCCCC[C@@H](O)CC(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
79240
PubChem CID
86289829
SMID ID
bhas#40

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 1
Aromatic Rings 0
Rotatable Bonds 22
Van der Waals Molecular Volume 539.49
Topological Polar Surface Area 118.52
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 7
logP 7.43
Molar Refractivity 141.33

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Created at
12th Jun 2020
Updated at
12th Jun 2020