Structure Database (LMSD)

Common Name
N-(3-hydroxy-octadecanoyl)-homoserine lactone
Systematic Name
N-(3-hydroxy-octadecanoyl)-homoserine lactone
Synonyms
  • 3OH-C18-HSL
LM ID
LMFA08030011
Formula
C22H41NO4
Exact Mass
Calculate m/z
383.303559
Status
Curated
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]
Hydroxy fatty acids [FA0105]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rhodovulum sulfidophilum (#35806)
Alphaproteobacteria (#28211)
Identification of novel long chain N-acylhomoserine lactones of chain length C20 from the marine phototrophic bacterium Rhodovulum sulfidophilum.,
Biosci Biotechnol Biochem, 2018
Pubmed ID: 30001674

String Representations

InChiKey (Click to copy)
IHJILWQXHBSFMS-ANYOKISRSA-N
InChi (Click to copy)
InChI=1S/C22H41NO4/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/h19-20,24H,2-18H2,1H3,(H,23,25)/t19?,20-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(O)CCCCCCCCCCCCCCC

Other Databases

CHEBI ID
187212
PubChem CID
138454227

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 17
Van der Waals Molecular Volume 417.68
Topological Polar Surface Area 77.70
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 5.51
Molar Refractivity 109.96

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Created at
-
Updated at
6th Feb 2021