Structure Database (LMSD)

Common Name
N-(3-oxo-11Z-octadecenoyl)-homoserine lactone
Systematic Name
N-(3-oxo-11Z-octadecenoyl)-homoserine lactone
Synonyms
  • 3O-C18:1-HSL
LM ID
LMFA08030020
Formula
C22H37NO4
Exact Mass
Calculate m/z
379.272259
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Fatty acyl homoserine lactones [FA0803]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Oxo fatty acids [FA0106]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sinorhizobium meliloti (#382)
Alphaproteobacteria (#28211)
Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-acyl homoserine lactones.,
J Bacteriol, 2002
Pubmed ID: 12270827

String Representations

InChiKey (Click to copy)
GVICTYCNLVDGLY-AQWUKCDYSA-N
InChi (Click to copy)
InChI=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 (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(=O)CCCCCCC/C=C\CCCCCC

Other Databases

CHEBI ID
187732
PubChem CID
138454228

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 412.40
Topological Polar Surface Area 74.54
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 5.21
Molar Refractivity 108.35

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Updated at
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