Structure database (LMSD)

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LM IDLMFA13040030
Common Nameascr#23
Systematic Name13R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-tetradecenoic acid
Synonyms13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-
tetradecenoic acid
Exact Mass
372.2512 (neutral)    Calculate m/z:
FormulaC20H36O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289694
CHEBI ID78961
InChIKeyVZEGHYGOTDETNP-VKEQHCKMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C20H36O6/c1-15(25-20-18(22)14-17(21)16(2)26-20)12-10-8-6-4-3-5-7-9-11-13-19(23)24/h11,13,15-18,20-22H,3-10,12,14H2,1-2H3,(H,23,24)/b13-11+/t15-,16+,17-,18-,20-/m1/s1
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SMILES
O([C@@H](CCCCCCCCC/C=C/C(=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 Atoms26Rings1Aromatic Rings0Rotatable Bonds13
 van der Waals
Molecular Volume
389.66Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP4.83Molar
Refractivity
102.40