Structure Database (LMSD)

H H H H H OH HO OH O O O O
Common Name
Withalongolide C
Systematic Name
5β,6β:22R,26-diepoxyergosta-4β,11β,19,27-tetrahydroxy-2,24-diene-1,26-dione
Synonyms
  • 11 Beta-Hydroxywithaferin A
LM ID
LMST01160055
Formula
C28H38O7
Exact Mass
Calculate m/z
486.261755
Sum Composition
ST 28:6;O7
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)
UPRPPTFVJBNIPP-VAPFTTHESA-N
InChi (Click to copy)
InChI=1S/C28H38O7/c1-13-9-20(34-25(33)16(13)12-29)14(2)17-5-6-18-15-10-23-28(35-23)22(32)8-7-21(31)27(28,4)24(15)19(30)11-26(17,18)3/h7-8,14-15,17-20,22-24,29-30,32H,5-6,9-12H2,1-4H3/t14-,15-,17+,18-,19-,20+,22-,23+,24+,26+,27+,28+/m0/s1
SMILES (Click to copy)
O1[C@@H]2C[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)[C@@]5([H])CC(C)=C(CO)C(=O)O5)[C@@]4(C)C[C@H](O)[C@]3([H])[C@]3(C(C=C[C@@H]([C@]132)O)=O)C

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
69108
PubChem CID
56926114

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 6
Aromatic Rings
Rotatable Bonds 3
Van der Waals Molecular Volume 469.77
Topological Polar Surface Area 118.66
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 4.04
Molar Refractivity 128.90

Admin

Created at
17th Dec 2021
Updated at
6th Dec 2023