Structure Database (LMSD)

Common Name
ascr#24
Systematic Name
13R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tetradecanoic acid
Synonyms
  • 13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acid
LM ID
LMFA13040029
Formula
C20H38O6
Exact Mass
Calculate m/z
374.26684
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)
NRXYKCLIMLPUIO-KWXDATOUSA-N
InChi (Click to copy)
InChI=1S/C20H38O6/c1-15(25-20-18(22)14-17(21)16(2)26-20)12-10-8-6-4-3-5-7-9-11-13-19(23)24/h15-18,20-22H,3-14H2,1-2H3,(H,23,24)/t15-,16+,17-,18-,20-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCC(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78962
PubChem CID
86289695
SMID ID
ascr#24

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 1
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 392.30
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 5.06
Molar Refractivity 102.50

Admin

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