Structure Database (LMSD)

Common Name
icos#1
Systematic Name
7-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-heptanoic acid
Synonyms
  • 7-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heptanoic acid
LM ID
LMFA13040132
Formula
C22H29NO7
Exact Mass
Calculate m/z
419.194404
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)
JPMANLDTTFCEPQ-XYHOUYMGSA-N
InChi (Click to copy)
InChI=1S/C22H29NO7/c1-14-19(30-21(27)16-13-23-17-9-6-5-8-15(16)17)12-18(24)22(29-14)28-11-7-3-2-4-10-20(25)26/h5-6,8-9,13-14,18-19,22-24H,2-4,7,10-12H2,1H3,(H,25,26)/t14-,18+,19+,22+/m0/s1
SMILES (Click to copy)
O(CCCCCCC(=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
79111
PubChem CID
86289757
SMID ID
icos#1

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 2
Rotatable Bonds 11
Van der Waals Molecular Volume 386.97
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 4.51
Molar Refractivity 111.60

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