Structure Database (LMSD)

Common Name
hbas#9
Systematic Name
4R-(3,6-dideoxy-(4-O-hydroxybenzoyl)α-L-arabino-hexopyranosyloxy)-pentanoic acid
Synonyms
  • 4R-(3'R-hydroxy-5'R-O-(4-hydroxybenzoyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentanoic acid
LM ID
LMFA13040149
Formula
C18H24O8
Exact Mass
Calculate m/z
368.14712
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)
GOULJBFAJHFZIY-WJOFSXDMSA-N
InChi (Click to copy)
InChI=1S/C18H24O8/c1-10(3-8-16(21)22)24-18-14(20)9-15(11(2)25-18)26-17(23)12-4-6-13(19)7-5-12/h4-7,10-11,14-15,18-20H,3,8-9H2,1-2H3,(H,21,22)/t10-,11+,14-,15-,18-/m1/s1
SMILES (Click to copy)
O([C@@H](CCC(=O)O)C)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CC=C(O)C=C2)[C@H](C)O1

Other Databases

PubChem CID
171120328
SMID ID
hbas#9

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 2
Aromatic Rings 1
Rotatable Bonds 8
Van der Waals Molecular Volume 341.46
Topological Polar Surface Area 124.59
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 3.12
Molar Refractivity 92.25

Admin

Created at
15th Jun 2020
Updated at
15th Jun 2020