Structure Database (LMSD)

Common Name
ibho#20
Systematic Name
3R-hydroxy-12-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-dodecanoic acid
Synonyms
  • 3R-hydroxy-12-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acid
LM ID
LMFA13040143
Formula
C27H39NO8
Exact Mass
Calculate m/z
505.267569
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)
PQBBEOSMILPNLI-NKVODUSASA-N
InChi (Click to copy)
InChI=1S/C27H39NO8/c1-18-24(36-26(33)21-17-28-22-13-9-8-12-20(21)22)16-23(30)27(35-18)34-14-10-6-4-2-3-5-7-11-19(29)15-25(31)32/h8-9,12-13,17-19,23-24,27-30H,2-7,10-11,14-16H2,1H3,(H,31,32)/t18-,19+,23+,24+,27+/m0/s1
SMILES (Click to copy)
O(CCCCCCCCC[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
79373
PubChem CID
86289899
SMID ID
ibho#20

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 3
Aromatic Rings 2
Rotatable Bonds 16
Van der Waals Molecular Volume 482.26
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 5.72
Molar Refractivity 136.59

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