Structure Database (LMSD)

Common Name
ascr#13
Systematic Name
7R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-octenoic acid
Synonyms
  • 7R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-octenoic acid
LM ID
LMFA13040037
Formula
C14H24O6
Exact Mass
Calculate m/z
288.15729
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)
OZXQOEFFYWNZJI-UYWLPYIRSA-N
InChi (Click to copy)
InChI=1S/C14H24O6/c1-9(6-4-3-5-7-13(17)18)19-14-12(16)8-11(15)10(2)20-14/h5,7,9-12,14-16H,3-4,6,8H2,1-2H3,(H,17,18)/b7-5+/t9-,10+,11-,12-,14-/m1/s1
SMILES (Click to copy)
O([C@@H](CCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78851
PubChem CID
86289665
SMID ID
ascr#13

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 1
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 285.86
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 2.49
Molar Refractivity 74.70

Admin

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