Structure Database (LMSD)

OH O OH O O O O O
Common Name
Berkeleylactone D
Systematic Name
4-[[(3E,6S,14R,16R)-14-hydroxy-16-methyl-2,5-dioxo-1-oxacyclohexadec-3-en-6-yl]oxy]-4-oxobutanoic acid
Synonyms
LM ID
LMFA07040164
Formula
C20H30O8
Exact Mass
Calculate m/z
398.19407
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)
MCGAXEIZZWCGNE-UYIHBRTKSA-N
InChi (Click to copy)
InChI=1S/C20H30O8/c1-14-13-15(21)7-5-3-2-4-6-8-17(16(22)9-11-19(25)27-14)28-20(26)12-10-18(23)24/h9,11,14-15,17,21H,2-8,10,12-13H2,1H3,(H,23,24)/b11-9+/t14-,15-,17+/m1/s1
SMILES (Click to copy)
C1([C@@H](OC(=O)CCC(=O)O)CCCCCCC[C@@H](O)C[C@@H](C)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
132967552

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings
Rotatable Bonds 5
Van der Waals Molecular Volume 399.32
Topological Polar Surface Area 129.27
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 8
logP 3.17
Molar Refractivity 100.93

Admin

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