Structure Database (LMSD)

Common Name
ascr#9
Systematic Name
4R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)pentanoic acid
Synonyms
  • 4R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentanoic acid
LM ID
LMFA13040007
Formula
C11H20O6
Exact Mass
Calculate m/z
248.12599
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)
NZMXMOQNHSVRAJ-WNPHYYBUSA-N
InChi (Click to copy)
InChI=1S/C11H20O6/c1-6(3-4-10(14)15)16-11-9(13)5-8(12)7(2)17-11/h6-9,11-13H,3-5H2,1-2H3,(H,14,15)/t6-,7+,8-,9-,11-/m1/s1
SMILES (Click to copy)
O([C@@H](CCC(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
79018
PubChem CID
71514783
SMID ID
ascr#9

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 1
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 236.60
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 1.54
Molar Refractivity 60.94

Admin

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