Structure Database (LMSD)

Common Name
N-(3R-hydroxy-7Z-tetradecenoyl)-homoserine lactone
Systematic Name
N-(3R-hydroxy-7Z-tetradecenoyl)-homoserine lactone
Synonyms
  • N-(3R-Hydroxy-7-cis-tetradecenoyl)homoserine lactone
LM ID
LMFA08030007
Formula
C18H31NO4
Exact Mass
Calculate m/z
325.225309
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]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rhizobium leguminosarum (#384)
Alphaproteobacteria (#28211)
Bacteriocin small of Rhizobium leguminosarum belongs to the class of N-acyl-L-homoserine lactone molecules, known as autoinducers and as quorum sensing co-transcription factors.,
J. Bacteriol, 1996
Pubmed ID: 8550454

String Representations

InChiKey (Click to copy)
GFSFGXWHLLUVRK-KTYGHDLGSA-N
InChi (Click to copy)
InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h7-8,15-16,20H,2-6,9-14H2,1H3,(H,19,21)/b8-7-/t15-,16+/m1/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)C[C@H](O)CCC/C=C\CCCCCC

Other Databases

KEGG ID
C11845
PubChem CID
24881364

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 345.84
Topological Polar Surface Area 77.70
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 3.72
Molar Refractivity 91.39

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Created at
-
Updated at
27th Nov 2020