Structure Database (LMSD)

Common Name
Berkeleylactone !
Systematic Name
4-oxo-5S-succinyl-12-hydroxy-15R-hexadeca-3E-enolide
Synonyms
LM ID
LMFA07040169
Formula
C20H30O8
Exact Mass
Calculate m/z
398.19407
Status
Active
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 turbatum (#70105)
Eurotiomycetes (#147545)
Berkeleylactones and a Citreohybriddione Analogue from Penicillium turbatum.,
J Nat Prod, 2021
Pubmed ID: 34851642

String Representations

InChiKey (Click to copy)
CQMHWNSCWQAFLH-CJVTYIJFSA-N
InChi (Click to copy)
InChI=1S/C20H30O8/c1-14-8-9-15(21)6-4-2-3-5-7-17(16(22)10-12-19(25)27-14)28-20(26)13-11-18(23)24/h10,12,14-15,17,21H,2-9,11,13H2,1H3,(H,23,24)/b12-10+/t14-,15?,17+/m1/s1
SMILES (Click to copy)
C1([C@@H](OC(=O)CCC(=O)O)CCCCCCC(O)CC[C@@H](C)OC(=O)C=C1)=O

Other Databases

PubChem CID
164620579

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
8th Dec 2021
Updated at
8th Dec 2021