Structure Database (LMSD)

Common Name
ascr#8
Systematic Name
N-(6R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-heptenoyl)-4-aminobenzoic acid
Synonyms
  • N-(6'R-[3''R,5''R-dihydroxy-6''S-methyl-(2H)-tetrahydropyran-2'-yloxy]-2'E-heptenoyl)-4-aminobenzoic acid
LM ID
LMFA13040154
Formula
C20H27NO7
Exact Mass
Calculate m/z
393.178754
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)
A Shortcut to Identifying Small Molecule Signals That Regulate Behavior and Development in Caenorhabditis Elegans,
Proc Natl Acad Sci U S A, 2009
Pubmed ID: 19346493

String Representations

InChiKey (Click to copy)
WMKIQPAVTRWYKZ-XPUFHXNMSA-N
InChi (Click to copy)
InChI=1S/C20H27NO7/c1-12(27-20-17(23)11-16(22)13(2)28-20)5-3-4-6-18(24)21-15-9-7-14(8-10-15)19(25)26/h4,6-10,12-13,16-17,20,22-23H,3,5,11H2,1-2H3,(H,21,24)(H,25,26)/b6-4+/t12-,13+,16-,17-,20-/m1/s1
SMILES (Click to copy)
O([C@@H](CC/C=C/C(=O)NC1=CC=C(C(=O)O)C=C1)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78834
PubChem CID
86289660
SMID ID
ascr#8

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 2
Aromatic Rings 1
Rotatable Bonds 8
Van der Waals Molecular Volume 375.63
Topological Polar Surface Area 127.39
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 8
logP 3.35
Molar Refractivity 104.48

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Created at
25th Jun 2020
Updated at
28th Oct 2021