Structure Database (LMSD)

Common Name
N-(3-hydroxy-9Z-hexadecenoyl)-homoserine lactone
Systematic Name
N-(3-hydroxy-9Z-hexadecenoyl)-homoserine lactone
Synonyms
  • 9-cis-3-OH-C16-HSL
LM ID
LMFA08030052
Formula
C20H35NO4
Exact Mass
Calculate m/z
353.256609
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]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Paraburkholderia tropica (#92647)
Betaproteobacteria (#28216)
Structural characterization of N-acyl-homoserine lactones from bacterial quorum sensing using LC-MS/MS analyses after Paternò-Büchi derivatization in solution.,
Anal Bioanal Chem, 2024
Pubmed ID: 38842688

String Representations

InChiKey (Click to copy)
YYPZVIJDOBLYTP-FYWLCUKRSA-N
InChi (Click to copy)
InChI=1S/C20H35NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(22)16-18(23)21-19-14-15-20(24)25-19/h7-8,17,19,22H,2-6,9-16H2,1H3,(H,21,23)/b8-7-/t17?,19-/m1/s1
SMILES (Click to copy)
C(CC(O)CCCCC/C=C\CCCCCC)(=O)N[C@@H]1OC(=O)CC1

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings
Rotatable Bonds 14
Van der Waals Molecular Volume 380.44
Topological Polar Surface Area 77.70
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 4.57
Molar Refractivity 99.89

Admin

Created at
24th Jun 2024
Updated at
24th Jun 2024