Structure Database (LMSD)

Common Name
ascr#17
Systematic Name
10R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-undecenoic acid
Synonyms
  • 10R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-undecenoic acid
LM ID
LMFA13040033
Formula
C17H30O6
Exact Mass
Calculate m/z
330.20424
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

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)
NEVPBIQTDNVVMK-KUTOLYOMSA-N
InChi (Click to copy)
InChI=1S/C17H30O6/c1-12(9-7-5-3-4-6-8-10-16(20)21)22-17-15(19)11-14(18)13(2)23-17/h8,10,12-15,17-19H,3-7,9,11H2,1-2H3,(H,20,21)/b10-8+/t12-,13+,14-,15-,17-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78952
PubChem CID
86289688
SMID ID
ascr#17

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 337.76
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.66
Molar Refractivity 88.55

Admin

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