4-epi-Withaferin A

ID: ALA3234482

Chembl Id: CHEMBL3234482

PubChem CID: 90670450

Max Phase: Preclinical

Molecular Formula: C28H38O6

Molecular Weight: 470.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1

Standard 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

Standard InChI Key:  DBRXOUCRJQVYJQ-SKXGSRCNSA-N

Alternative Forms

1. Parent:

   

   ALA3234482

   4-epi-Withaferin A

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 470.61

Molecular Weight (Monoisotopic): 470.2668

AlogP: 3.35

#Rotatable Bonds: 3

Polar Surface Area: 96.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.44

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: 3.88

References

1. Wijeratne EM, Xu YM, Scherz-Shouval R, Marron MT, Rocha DD, Liu MX, Costa-Lotufo LV, Santagata S, Lindquist S, Whitesell L, Gunatilaka AA..  (2014)  Structure-activity relationships for withanolides as inducers of the cellular heat-shock response.,  57  (7): [PMID:24625088] [10.1021/jm401279n]

2. Wijeratne EMK, Oliveira MCF, Mafezoli J, Xu YM, Minguzzi S, Batista PHJ, Pessoa ODL, Whitesell L, Gunatilaka AAL..  (2018)  Withaferin A and Withanolide D Analogues with Dual Heat-Shock-Inducing and Cytotoxic Activities: Semisynthesis and Biological Evaluation.,  81  (4): [PMID:29537263] [10.1021/acs.jnatprod.7b00918]

Source

Source(1):

• Scientific Literature