Structure database (LMSD)

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LM IDLMST01160019
Common NameWithanolide A
Systematic Name15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-
10,14-dimethyl-3-oxapentacyclo[9.7.0.0ω{2,4}.0ω{5,10}.0ω{14,18}]octadec-7-en-9-
one
Synonyms-
Exact Mass
470.2668 (neutral)    Calculate m/z:
FormulaC28H38O6
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassWithanolides and derivatives [ST0116]
AbbrevST 28:6;O6
PubChem CID14236710
HMDB IDHMDB0034415
CAYMAN ID11797
InChIKeyDXWHOKCXBGLTMQ-SFQAJKIESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1
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SMILES
O1C(=O)C(C)=C(C)C[C@]1([H])[C@](O)([C@]1([H])[C@@]2(C)CC[C@@]3([H])[C@@]([H])([C@@H]4O[C@@H]4[C@@]4(O)CC=CC(=O)[C@@]43C)[C@]2([H])CC1)C
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StatusActive
ReferencesWithanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.
Chem Pharm Bull (Tokyo), 2002
DOI: 10.1248/cpb.50.760
PMID: 12045329
Calculated physicochemical properties (?):
 Heavy Atoms34Rings6Aromatic Rings0Rotatable Bonds2
 van der Waals
Molecular Volume
460.98Topological Polar
Surface Area
98.43Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
6
 logP4.93Molar
Refractivity
127.07