Structure Database (LMSD)

Common Name
Berkeleylactone F
Systematic Name
4R,5S,14S-trihydroxy-15R-hexadeca-3E-enolide
Synonyms
  • (3E,5R,6S,15S,16R)-5,6,15-trihydroxy-16-methyl-1-oxacyclohexadec-3-en-2-on
LM ID
LMFA07040166
Formula
C16H28O5
Exact Mass
Calculate m/z
300.193675
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)
OXTXYWGSTRVDDS-MLCUHWOYSA-N
InChi (Click to copy)
InChI=1S/C16H28O5/c1-12-13(17)8-6-4-2-3-5-7-9-14(18)15(19)10-11-16(20)21-12/h10-15,17-19H,2-9H2,1H3/b11-10+/t12-,13+,14+,15-/m1/s1
SMILES (Click to copy)
[C@@H]1([C@@H](O)CCCCCCCC[C@H](O)[C@@H](C)OC(=O)C=C1)O

Other Databases

PubChem CID
132967554

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings
Rotatable Bonds
Van der Waals Molecular Volume 311.67
Topological Polar Surface Area 89.06
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 2.84
Molar Refractivity 81.70

Admin

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