Structure Database (LMSD)

Common Name
Berkeleylactone G
Systematic Name
5S-succinyl-4R,14S-dihydroxy-15R-hexadeca-3E-enolide
Synonyms
  • 4-[[(3E,5R,6S,15S,16R)-5,15-dihydroxy-16-methyl-2-oxo-1-oxacyclohexadec-3-en-6-yl]oxy]-4-oxobutanoic acid
LM ID
LMFA07040167
Formula
C20H32O8
Exact Mass
Calculate m/z
400.20972
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

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

String Representations

InChiKey (Click to copy)
LHCHMGFKQQZRRH-JUDWWFKISA-N
InChi (Click to copy)
InChI=1S/C20H32O8/c1-14-15(21)8-6-4-2-3-5-7-9-17(16(22)10-12-19(25)27-14)28-20(26)13-11-18(23)24/h10,12,14-17,21-22H,2-9,11,13H2,1H3,(H,23,24)/b12-10+/t14-,15+,16-,17+/m1/s1
SMILES (Click to copy)
[C@@H]1([C@@H](OC(=O)CCC(=O)O)CCCCCCCC[C@H](O)[C@@H](C)OC(=O)C=C1)O

Other Databases

PubChem CID
132967555

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings
Rotatable Bonds 5
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