Structure Database (LMSD)

Common Name
ibha#28
Systematic Name
3R-hydroxy-15R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-hexadecanoic acid
Synonyms
  • 3R-hydroxy-15R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexadecanoic acid
LM ID
LMFA13040108
Formula
C31H47NO8
Exact Mass
Calculate m/z
561.330169
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)
DVKTXYSVNVCEOI-AQTHURGKSA-N
InChi (Click to copy)
InChI=1S/C31H47NO8/c1-21(14-10-8-6-4-3-5-7-9-11-15-23(33)18-29(35)36)38-31-27(34)19-28(22(2)39-31)40-30(37)25-20-32-26-17-13-12-16-24(25)26/h12-13,16-17,20-23,27-28,31-34H,3-11,14-15,18-19H2,1-2H3,(H,35,36)/t21-,22+,23+,27-,28-,31-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCC[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
79359
PubChem CID
86289894
SMID ID
ibha#28

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 3
Aromatic Rings 2
Rotatable Bonds 19
Van der Waals Molecular Volume 551.46
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 7.28
Molar Refractivity 155.06

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