Structure database (LMSD)

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LM IDLMFA13040049
Common Namebhas#24
Systematic Name3R-hydroxy-13R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tetradecanoic acid
Synonyms3R-hydroxy-13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-
tetradecanoic acid
Exact Mass
390.2618 (neutral)    Calculate m/z:
FormulaC20H38O7
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289821
CHEBI ID79232
InChIKeyUXIWWNCPRZIUAB-XGZVRMHOSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C20H38O7/c1-14(26-20-18(23)13-17(22)15(2)27-20)10-8-6-4-3-5-7-9-11-16(21)12-19(24)25/h14-18,20-23H,3-13H2,1-2H3,(H,24,25)/t14-,15+,16-,17-,18-,20-/m1/s1
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SMILES
O([C@@H](CCCCCCCCC[C@@H](O)CC(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1
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StatusActive
ReferencesBiosynthesis of the Caenorhabditis Elegans Dauer Pheromone
Proc Natl Acad Sci U S A. 2009
DOI: 10.1073/pnas.0810338106
PMID: 19174521
Calculated physicochemical properties (?):
 Heavy Atoms27Rings1Aromatic Rings0Rotatable Bonds14
 van der Waals
Molecular Volume
401.09Topological Polar
Surface Area
118.52Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
7
 logP4.31Molar
Refractivity
104.40