Structure Database (LMSD)

Common Name
Withaferin A
Systematic Name
5β,6β:22R,26-diepoxyergosta-4β,27-dihydroxy-2,24-diene-1,26-dione
Synonyms
  • Withaferine A
  • NSC101088
  • NSC 273757
  • WITHAFERIN DERIV JPR, IOWA U. COMPOUND
  • NSC-101088
LM ID
LMST01160017
Formula
C28H38O6
Exact Mass
Calculate m/z
470.26684
Sum Composition
ST 28:6;O6
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Acnistus arborescens (#362341)
Magnoliopsida (#3398)
Tumor inhibitors. XXXIX. Active principles of Acnistus arborescens. Isolation and structural and spectral studies of withaferin A and withacnistin.,
J Org Chem, 1969
Pubmed ID: 5357526

String Representations

InChiKey (Click to copy)
DBRXOUCRJQVYJQ-CKNDUULBSA-N
InChi (Click to copy)
InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,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)CC[C@]3([H])[C@]3(C(C=C[C@@H]([C@]132)O)=O)C

Other Databases

Wikipedia
Withaferin_A
KEGG ID
C08841
CHEBI ID
69120
PubChem CID
265237
GuidePharm ID
13097

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 6
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 460.98
Topological Polar Surface Area 98.43
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 6
logP 4.78
Molar Refractivity 127.00

Admin

Created at
-
Updated at
17th Dec 2021