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Withaferin A information


Withaferin A
Names
IUPAC name
(22R)-4β,27-Dihydroxy-5,6β:22,26-diepoxy-5β-ergosta-2,24-diene-1,26-dione
Systematic IUPAC name
(4S,4aR,5aR,6aS,6bS,9R,9aS,11aS,11bR)-4-Hydroxy-9-{(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one
Other names
Withaferine A
Identifiers
CAS Number
  • 5119-48-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:69120
ChEMBL
  • ChEMBL1221986
ChemSpider
  • 233064
PubChem CID
  • 265237
UNII
  • L6DO3QW4K5 checkY
CompTox Dashboard (EPA)
  • DTXSID10965459 Edit this at Wikidata
InChI
  • 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
    Key: DBRXOUCRJQVYJQ-CKNDUULBSA-N
  • InChI=1/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
    Key: DBRXOUCRJQVYJQ-CKNDUULBBI
SMILES
  • O=C/1O[C@H](CC(=C\1CO)\C)[C@@H](C)[C@H]6CC[C@@H]4[C@]6(C)CC[C@@H]3[C@]5(C(=O)\C=C/[C@H](O)[C@]52O[C@@H]2C[C@H]34)C
Properties
Chemical formula
 C28H38O6
Molar mass 470.606 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Withaferin A is a steroidal lactone, derived from Acnistus arborescens,[1] Withania somnifera[2] and other members of family Solanaceae. It is the first member of the withanolide class of ergostane type product to be discovered.

  1. ^ Kupchan, S. M.; Anderson, W. K.; Bollinger, P.; Doskotch, R. W.; Smith, R. M.; Renauld, J. A.; Schnoes, H. K.; Burlingame, A. L.; Smith, D. H. (1969-12-01). "Tumor inhibitors. XXXIX. Active principles of Acnistus arborescens. Isolation and structural and spectral studies of withaferin A and withacnistin". The Journal of Organic Chemistry. 34 (12): 3858–3866. doi:10.1021/jo01264a027. PMID 5357526.
  2. ^ Cite error: The named reference with2004 was invoked but never defined (see the help page).

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Withaferin A

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Withaferin A is a steroidal lactone, derived from Acnistus arborescens, Withania somnifera and other members of family Solanaceae. It is the first member...

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Withanolide

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date. Withaferin A, the first withanolide to be isolated, was found in winter cherry (Withania somnifera) and Acnistus arborescens. Salpichrolides A, B and...

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somnifera are withanolides, a group of triterpene lactones that include withaferin A, alkaloids, steroidal lactones, tropine, and cuscohygrine. Forty withanolides...

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an antineoplastic antibiotic produced by Streptomyces plicatus, and Withaferin A, a steroidal lactone from Withania somnifera plant are known to inhibit...

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commonly known as Ashwagandha, and the team identified Withanolide, Withaferin A and Withanone as the three steroidal contents of the plant which gives...

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