Structure database (LMSD)

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LM IDLMFA08030020
Common NameN-(3-oxo-11Z-octadecenoyl)-homoserine lactone
Systematic NameN-(3-oxo-11Z-octadecenoyl)-homoserine lactone
Synonyms3O-C18:1-HSL
Exact Mass
379.2723 (neutral)    Calculate m/z:
FormulaC22H37NO4
CategoryFatty Acyls [FA]
Main ClassFatty amides [FA08]
Sub ClassFatty acyl homoserine lactones [FA0803]
Alternative ClassesUnsaturated fatty acids[FA0103], Oxo fatty acids[FA0106]
PubChem CID-
InChIKeyGVICTYCNLVDGLY-AQWUKCDYSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C22H37NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(24)18-21(25)23-20-16-
17-27-22(20)26/h7-8,20H,2-6,9-18H2,1H3,(H,23,25)/b8-7-/t20-/m0/s1
SMILES[C@@H]1(CCOC1=O)NC(=O)CC(=O)CCCCCCC/C=C\CCCCCC
StatusActive
ReferencesCharacterization of the Sinorhizobium meliloti sinR/sinI Locus and the Production of Novel N-Acyl Homoserine Lactones. Melanie M. Marketon, Matthew R. Gronquist, Anatol Eberhard and Juan E. González. Journal of Bacteriology. Volume 184. Issue 20, 2002, pp. 5686–5695. doi: 10.1128/JB.184.20.5686-5695.2002

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC139616/
Calculated physicochemical properties (?):
 Heavy Atoms27Rings1Aromatic Rings0Rotatable Bonds16
 van der Waals
Molecular Volume
412.40Topological Polar
Surface Area
74.54Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
5
 logP5.21Molar
Refractivity
108.35