Structure database (LMSD)

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LM IDLMST01160012
Common NamePhysalolactone
Systematic Name17S,20S,22R-6α-chloro-4β,5β,17β,14α,20α-pentahydroxy-1-oxo-ergosta-2,24-
dienolide
Synonyms-
Exact Mass
538.2333 (neutral)    Calculate m/z:
FormulaC28H39O8Cl
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassWithanolides and derivatives [ST0116]
PubChem CID5458763
HMDB IDHMDB0034333
InChIKeyXCJUXWOCLLPHII-UXKAJNCKSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H39ClO8/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-18(29)28(36)20(31)7-6-19(30)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-18,20-21,31,33-36H,8-13H2,1-5H3/t16-,17+,18-,20-,21+,23-,24-,25-,26+,27-,28-/m0/s1
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SMILES
[C@@]12(O)CC[C@@](O)([C@](O)(C)[C@]3([H])OC(=O)C(C)=C(C)C3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H]([C@]2(O)[C@@H](O)C=CC([C@]12C)=O)Cl
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StatusActive
ReferencesPhysalolactone C, a New Withanolide from Physalis peruviana
J. Nat. Prod. 1984
DOI: 10.1021/np50034a013
Calculated physicochemical properties (?):
 Heavy Atoms37Rings5Aromatic Rings0Rotatable Bonds2
 van der Waals
Molecular Volume
506.13Topological Polar
Surface Area
146.59Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
8
 logP3.93Molar
Refractivity
138.00