Structure Database (LMSD)

Common Name
ibha#30
Systematic Name
3R-hydroxy-16R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-heptadecanoic acid
Synonyms
  • 3R-hydroxy-16R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heptadecanoic acid
LM ID
LMFA13040107
Formula
C32H49NO8
Exact Mass
Calculate m/z
575.345819
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)
RHGNPNMYKQDMAV-VHJGPELESA-N
InChi (Click to copy)
InChI=1S/C32H49NO8/c1-22(15-11-9-7-5-3-4-6-8-10-12-16-24(34)19-30(36)37)39-32-28(35)20-29(23(2)40-32)41-31(38)26-21-33-27-18-14-13-17-25(26)27/h13-14,17-18,21-24,28-29,32-35H,3-12,15-16,19-20H2,1-2H3,(H,36,37)/t22-,23+,24-,28-,29-,32-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCC[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
79360
PubChem CID
86289895
SMID ID
ibha#30

Calculated Physicochemical Properties

Heavy Atoms 41
Rings 3
Aromatic Rings 2
Rotatable Bonds 20
Van der Waals Molecular Volume 568.76
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 7.67
Molar Refractivity 159.68

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