Structure Database (LMSD)

OH H H H H H O OH HO O HO HO O O O
Common Name
Withalongolide M
Systematic Name
28-O-β-d-glucopyranosyl 22R,26-epoxy-19-norergosta-3β-hydroxy-5(10),24-diene-1,26-dione
Synonyms
  • 28-O-beta-d-glucopyranosyl-3beta-hydroxy-1-oxo-19-norwitha-5(10),24-dienolide
LM ID
LMST01160079
Formula
C33H48O10
Exact Mass
Calculate m/z
604.32475
Sum Composition
ST 27:5;O5;Hex
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Withanolides and derivatives [ST0116]

String Representations

InChiKey (Click to copy)
CLUVBNATYXEVRS-UJQMTUMNSA-N
InChi (Click to copy)
InChI=1S/C33H48O10/c1-15-18(14-41-32-30(39)29(38)28(37)26(13-34)43-32)11-25(42-31(15)40)16(2)22-6-7-23-20-5-4-17-10-19(35)12-24(36)27(17)21(20)8-9-33(22,23)3/h16,19-23,25-26,28-30,32,34-35,37-39H,4-14H2,1-3H3/t16-,19+,20+,21-,22+,23-,25+,26+,28+,29-,30+,32+,33+/m0/s1
SMILES (Click to copy)
O=C1C[C@H](O)CC2CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)[C@@]5([H])CC(CO[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)=C(C)C(=O)O5)[C@@]4(C)CC[C@]3([H])C=21

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Physalis longifolia (#161495)
Magnoliopsida (#3398)
Cytotoxic withanolide constituents of Physalis longifolia.,
J Nat Prod, 2011
Pubmed ID: 22098611

Other Databases

CHEBI ID
69117
PubChem CID
56926294

Calculated Physicochemical Properties

Heavy Atoms 43
Rings 6
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 582.64
Topological Polar Surface Area 167.12
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 10
logP 4.52
Molar Refractivity 157.69

Admin

Created at
6th Dec 2023
Updated at
6th Dec 2023