Structure Database (LMSD)

HO O O
Common Name
Berkeleylactone L
Systematic Name
4S-hydroxy-15R-hexadeca-3E-enolide
Synonyms
  • (3E,5S,16R)-5-hydroxy-16-methyl-1-oxacyclohexadec-3-en-2-one
LM ID
LMFA07040172
Formula
C16H28O3
Exact Mass
Calculate m/z
268.203845
Sum Composition
FA 16:2;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Lactones [FA0704]

String Representations

InChiKey (Click to copy)
JVNFUDLQCWWEEB-WCVFXIOZSA-N
InChi (Click to copy)
InChI=1S/C16H28O3/c1-14-10-8-6-4-2-3-5-7-9-11-15(17)12-13-16(18)19-14/h12-15,17H,2-11H2,1H3/b13-12+/t14-,15+/m1/s1
SMILES (Click to copy)
[C@@H]1(CCCCCCCCCC[C@@H](C)OC(=O)C=C1)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Penicillium turbatum (#70105)
Eurotiomycetes (#147545)
Berkeleylactones and a Citreohybriddione Analogue from Penicillium turbatum.,
J Nat Prod, 2021
Pubmed ID: 34851642

Other Databases

PubChem CID
135338051

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 1
Aromatic Rings
Rotatable Bonds
Van der Waals Molecular Volume 294.09
Topological Polar Surface Area 48.60
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 4.32
Molar Refractivity 77.89

Admin

Created at
8th Dec 2021
Updated at
8th Dec 2021