Structure Database (LMSD)

Common Name
ibho#24
Systematic Name
3R-hydroxy-14-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tetradecanoic acid
Synonyms
  • 3R-hydroxy-14-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acid
LM ID
LMFA13040145
Formula
C29H43NO8
Exact Mass
Calculate m/z
533.298869
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)
LXVPUPUKAHIWDZ-STNUDKPESA-N
InChi (Click to copy)
InChI=1S/C29H43NO8/c1-20-26(38-28(35)23-19-30-24-15-11-10-14-22(23)24)18-25(32)29(37-20)36-16-12-8-6-4-2-3-5-7-9-13-21(31)17-27(33)34/h10-11,14-15,19-21,25-26,29-32H,2-9,12-13,16-18H2,1H3,(H,33,34)/t20-,21+,25+,26+,29+/m0/s1
SMILES (Click to copy)
O(CCCCCCCCCCC[C@@H](O)CC(=O)O)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CNC3C=CC=CC=32)[C@H](C)O1

Other Databases

CHEBI ID
79375
PubChem CID
86289901
SMID ID
ibho#24

Calculated Physicochemical Properties

Heavy Atoms 38
Rings 3
Aromatic Rings 2
Rotatable Bonds 18
Van der Waals Molecular Volume 516.86
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 6.50
Molar Refractivity 145.82

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