Structure database (LMSD)

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LM IDLMST01160021
Common NameWithaperuvin B
Systematic Name17S,20S,22R-4β,5β,6α,17β,20α-pentahydroxy-1-oxo-ergosta-2,14,24-trienolide
Synonyms-
Exact Mass
502.2567 (neutral)    Calculate m/z:
FormulaC28H38O8
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassWithanolides and derivatives [ST0116]
AbbrevST 28:6;O8
PubChem CID3734964
HMDB IDHMDB0034191
InChIKeyIHIHXNCZVACPKN-WOONZQPCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H38O8/c1-14-12-22(36-23(32)15(14)2)26(5,33)27(34)11-9-17-16-13-21(31)28(35)20(30)7-6-19(29)25(28,4)18(16)8-10-24(17,27)3/h6-7,9,16,18,20-22,30-31,33-35H,8,10-13H2,1-5H3/t16-,18-,20-,21-,22+,24-,25-,26-,27-,28+/m0/s1
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SMILES
C1(=O)C=C[C@H](O)[C@@]2(O)[C@@H](O)C[C@@]3([H])C4=CC[C@@](O)([C@](O)(C)[C@]5([H])OC(=O)C(C)=C(C)C5)[C@@]4(C)CC[C@]3([H])[C@@]12C
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StatusActive
ReferencesStructures of Withaperuvin B and C, Withanolides of Physalis peruviana Roots
Heterocycles 1970
DOI: 10.3987/R-1982-01-0037
Calculated physicochemical properties (?):
 Heavy Atoms36Rings5Aromatic Rings0Rotatable Bonds2
 van der Waals
Molecular Volume
488.28Topological Polar
Surface Area
146.59Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
8
 logP3.20Molar
Refractivity
132.37