Structure Database (LMSD)

Common Name
ibha#16
Systematic Name
3R-hydroxy-9R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-decanoic acid
Synonyms
  • 3R-hydroxy-9R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acid
LM ID
LMFA13040114
Formula
C25H35NO8
Exact Mass
Calculate m/z
477.236269
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)
KNTSMTUFIKIJQO-HGAUGMLMSA-N
InChi (Click to copy)
InChI=1S/C25H35NO8/c1-15(8-4-3-5-9-17(27)12-23(29)30)32-25-21(28)13-22(16(2)33-25)34-24(31)19-14-26-20-11-7-6-10-18(19)20/h6-7,10-11,14-17,21-22,25-28H,3-5,8-9,12-13H2,1-2H3,(H,29,30)/t15-,16+,17+,21-,22-,25-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCC[C@H](O)CC(=O)O)C)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CNC3C=CC=CC=32)[C@H](C)O1

Other Databases

CHEBI ID
79353
PubChem CID
86289888
SMID ID
ibha#16

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 3
Aromatic Rings 2
Rotatable Bonds 13
Van der Waals Molecular Volume 447.66
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 4.94
Molar Refractivity 127.36

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Created at
14th Jun 2020
Updated at
14th Jun 2020