Structure Database (LMSD)

Common Name
Acutifolactone
Systematic Name
(22R,24S,25S)-5α-hydroxy-7α,8α;24α,25α-diepoxy-1,12,16-trioxowitha-2,17(20)-dienolide
Synonyms
LM ID
LMST01160031
Formula
C28H32O8
Exact Mass
Calculate m/z
496.20972
Sum Composition
ST 28:9;O8
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Withanolides and derivatives [ST0116]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Physalis acutifolia (#304134)
Magnoliopsida (#3398)
Cytotoxic Physalins from Aeroponically Grown Physalis acutifolia.,
J Nat Prod, 2021
Pubmed ID: 33586438

String Representations

InChiKey (Click to copy)
ZHKCPWIMFGFTGL-ZRKMWVMKSA-N
InChi (Click to copy)
InChI=1S/C28H32O8/c1-12(16-11-24(2)27(5,36-24)23(32)34-16)20-15(29)9-13-19-14(10-18(31)25(13,20)3)26(4)17(30)7-6-8-28(26,33)22-21(19)35-22/h6-7,13-14,16,19,21-22,33H,8-11H2,1-5H3/b20-12+/t13-,14-,16+,19-,21-,22-,24-,25+,26-,27+,28-/m0/s1
SMILES (Click to copy)
O=C1C=CC[C@]2(O)[C@H]3O[C@H]3[C@@]3([H])[C@]4([H])CC(=O)/C(=C(/C)\[C@]5([H])OC(=O)[C@@]6(C)O[C@@]6(C)C5)/[C@@]4(C)C(=O)C[C@]3([H])[C@]21C

Other Databases

PubChem CID
164621904

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 7
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 460.92
Topological Polar Surface Area 124.87
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 3.73
Molar Refractivity 126.47

Admin

Created at
17th Feb 2021
Updated at
17th Feb 2021