Structure Database (LMSD)

Common Name
Withalongolide L
Systematic Name
28-O-β-d-glucopyranosyl 22R,26-epoxy-19-norergosta-3β,6α-dihydroxy-5(10),24-diene-1,26-dione
Synonyms
  • 28-O-beta-d-glucopyranosyl-3beta,6alpha-dihydroxy-1-oxo-19-norwitha-5(10),24-dienolide
LM ID
LMST01160078
Formula
C33H48O11
Exact Mass
Calculate m/z
620.319665
Sum Composition
ST 27:5;O6;Hex
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

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

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

String Representations

InChiKey (Click to copy)
DKRAEDZNHJHJAB-YJKJOOOHSA-N
InChi (Click to copy)
InChI=1S/C33H48O11/c1-14-16(13-42-32-30(40)29(39)28(38)26(12-34)44-32)8-25(43-31(14)41)15(2)21-4-5-22-19-11-23(36)20-9-17(35)10-24(37)27(20)18(19)6-7-33(21,22)3/h15,17-19,21-23,25-26,28-30,32,34-36,38-40H,4-13H2,1-3H3/t15-,17+,18-,19+,21+,22-,23-,25+,26+,28+,29-,30+,32+,33+/m0/s1
SMILES (Click to copy)
O=C1C[C@H](O)CC2[C@@H](O)C[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

Other Databases

CHEBI ID
69116
PubChem CID
56926208

Calculated Physicochemical Properties

Heavy Atoms 44
Rings 6
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 591.43
Topological Polar Surface Area 187.35
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 11
logP 3.78
Molar Refractivity 159.59

Admin

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