Structure database (LMSD)

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LM IDLMST01160032
Common NameWithaperuvin
Systematic Name17S,20S,22R-4β,5β,6α,14α,17β,20α-hexahydroxy-1-oxo-ergosta-2,24-dienolide
Synonyms-
Exact Mass
520.2672 (neutral)    Calculate m/z:
FormulaC28H40O9
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassWithanolides and derivatives [ST0116]
AbbrevST 28:5;O9
PubChem CID333470
InChIKeyXLUKITCTLVOOAW-VQDSAXESSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H40O9/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-20(31)28(36)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30-31,33-36H,8-13H2,1-5H3/t16-,17+,19-,20-,21+,23-,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])[C@]4(O)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 Atoms37Rings5Aromatic Rings0Rotatable Bonds2
 van der Waals
Molecular Volume
499.71Topological Polar
Surface Area
166.82Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
9
 logP2.68Molar
Refractivity
134.37