Structure database (LMSD)

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LM IDLMST01160010
Common Name4β-Hydroxywithanolide E
Systematic Name15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,12,15-
trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0ω{2,7}.0ω{7,9}.0ω{12,
16}]octadec-4-en-3-one
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 CID73621
HMDB IDHMDB0034059
CAYMAN ID27245
InChIKeyUPBUGICUKQIKTJ-KABTZXSUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H38O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30,32-34H,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@@]23O[C@@H]2C[C@@]2([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@]2([H])[C@@]13C
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StatusActive
ReferencesIsolation of 4 beta-hydroxywithanolide E, a new withanolide from Physalis peruviana L.
Chem Pharm Bull (Tokyo), 1976
DOI: 10.1248/cpb.24.1403
PMID: 1021295
Calculated physicochemical properties (?):
 Heavy Atoms36Rings6Aromatic Rings0Rotatable Bonds2
 van der Waals
Molecular Volume
478.56Topological Polar
Surface Area
138.89Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
8
 logP3.73Molar
Refractivity
131.02