Structure Database (LMSD)

Common Name
Berkeleylactone A
Systematic Name
(2S)-2-hydroxy-3-[[(3R,6S,16R)-6-hydroxy-16-methyl-2,5-dioxo-oxacyclohexadec-3-yl]sulfanyl]propanoic acid
Synonyms
LM ID
LMFA07040161
Formula
C19H32O7S
Exact Mass
Calculate m/z
404.186877
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

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)
KQOUUXPIBXWEMV-YALNPMBYSA-N
InChi (Click to copy)
InChI=1S/C19H32O7S/c1-13-9-7-5-3-2-4-6-8-10-14(20)15(21)11-17(19(25)26-13)27-12-16(22)18(23)24/h13-14,16-17,20,22H,2-12H2,1H3,(H,23,24)/t13-,14+,16-,17-/m1/s1
SMILES (Click to copy)
C1(O[C@H](C)CCCCCCCCC[C@H](O)C(=O)C[C@H]1SC[C@@H](O)C(O)=O)=O

Other Databases

PubChem CID
132967549

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings
Rotatable Bonds 4
Van der Waals Molecular Volume 397.02
Topological Polar Surface Area 123.20
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 3.74
Molar Refractivity 105.16

Admin

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