Structure Database (LMSD)

HO O O HO O HO O O
Common Name
Berkeleylactone H
Systematic Name
5S-succinyl-4R,16-dihydroxy-15R-hexadeca-3E-enolide
Synonyms
  • 4-[[(3E,5R,6S,16S)-5-hydroxy-16-(hydroxymethyl)-2-oxo-1-oxacyclohexadec-3-en-6-yl]oxy]-4-oxobutanoic acid
LM ID
LMFA07040168
Formula
C20H32O8
Exact Mass
Calculate m/z
400.20972
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)
VWUDIRRHACQVQE-XOZUALGNSA-N
InChi (Click to copy)
InChI=1S/C20H32O8/c21-14-15-8-6-4-2-1-3-5-7-9-17(16(22)10-12-19(25)27-15)28-20(26)13-11-18(23)24/h10,12,15-17,21-22H,1-9,11,13-14H2,(H,23,24)/b12-10+/t15-,16+,17-/m0/s1
SMILES (Click to copy)
[C@@H]1([C@@H](OC(=O)CCC(=O)O)CCCCCCCCC[C@@H](CO)OC(=O)C=C1)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Penicillium fuscum (#70104)
Eurotiomycetes (#147545)
The Berkeleylactones, Antibiotic Macrolides from Fungal Coculture.,
J Nat Prod, 2017
Pubmed ID: 28326781

Other Databases

PubChem CID
132967556

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 401.96
Topological Polar Surface Area 132.43
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 3.25
Molar Refractivity 102.44

Admin

Created at
7th Dec 2021
Updated at
8th Dec 2021