Summary

IMPPAT Phytochemical identifier: IMPHY004118

Phytochemical name: Withaferin A

Synonymous chemical names:
4β,27-dihydroxy-1-oxo-5β,6β-epoxy-20r, 22r-witha-2,24-dienolide (withaferin a), withaferin a, withaferin-a, withaniol

External chemical identifiers:
CID:265237, ChEMBL:CHEMBL517080, ChEBI:69120, ZINC:ZINC000008234189, FDASRS:L6DO3QW4K5, SureChEMBL:SCHEMBL157208, MolPort-006-822-486

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Chemical structure information

SMILES:
OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C

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

InChIKey:
DBRXOUCRJQVYJQ-CKNDUULBSA-N

DeepSMILES:
OCC=CC)C[C@@H]OC6=O)))[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6C[C@@H][C@][C@]6C)C=O)C=C[C@@H]6O))))))O3)))))))))))))C

Functional groups:
CC1=C(C)C(=O)OCC1, CC=CC(C)=O, CO, C[C@H]1O[C@@]1(C)C

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C=CCC(CC2CCC3C2CCC2C3CC3OC34CC=CC(=O)C24)O1

Scaffold Graph/Node level:
OC1CCCC(CC2CCC3C2CCC2C3CC3OC34CCCC(O)C24)O1

Scaffold Graph level:
CC1CCCC(CC2CCC3C2CCC2C3CC3CC34CCCC(C)C24)C1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Steroids and steroid derivatives

ClassyFire Subclass: Steroid lactones

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Steroids

NP Classifier Class: Ergostane steroids

NP-Likeness score: 3.881

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Chemical structure download