Structure Database (LMSD)

Common Name
ascr#25
Systematic Name
14R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-pentadecanoic acid
Synonyms
  • 14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-pentadecanoic acid
LM ID
LMFA13040012
Formula
C21H38O6
Exact Mass
Calculate m/z
386.26684
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)
MTVUVHUAEUQKIN-YWWXTUTHSA-N
InChi (Click to copy)
InChI=1S/C21H38O6/c1-16(26-21-19(23)15-18(22)17(2)27-21)13-11-9-7-5-3-4-6-8-10-12-14-20(24)25/h12,14,16-19,21-23H,3-11,13,15H2,1-2H3,(H,24,25)/b14-12+/t16-,17+,18-,19-,21-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78963
PubChem CID
86289696
SMID ID
ascr#25

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 406.96
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 5.22
Molar Refractivity 107.02

Admin

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