Structure Database (LMSD)

Common Name
ascr#27
Systematic Name
15R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-hexadecenoic acid
Synonyms
  • 15R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-hexadecenoic acid
LM ID
LMFA13040026
Formula
C22H40O6
Exact Mass
Calculate m/z
400.28249
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)
PHSQDXKUQRUWOG-PXMSNCRXSA-N
InChi (Click to copy)
InChI=1S/C22H40O6/c1-17(27-22-20(24)16-19(23)18(2)28-22)14-12-10-8-6-4-3-5-7-9-11-13-15-21(25)26/h13,15,17-20,22-24H,3-12,14,16H2,1-2H3,(H,25,26)/b15-13+/t17-,18+,19-,20-,22-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78965
PubChem CID
86289698
SMID ID
ascr#27

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 424.26
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 5.61
Molar Refractivity 111.64

Admin

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