4,27-diacetyl-4-epi-withaferin A

ID: ALA3234488

Chembl Id: CHEMBL3234488

PubChem CID: 90670456

Max Phase: Preclinical

Molecular Formula: C32H42O8

Molecular Weight: 554.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C)C[C@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@H](OC(C)=O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)OC1=O

Standard InChI:  InChI=1S/C32H42O8/c1-16-13-25(39-29(36)21(16)15-37-18(3)33)17(2)22-7-8-23-20-14-28-32(40-28)27(38-19(4)34)10-9-26(35)31(32,6)24(20)11-12-30(22,23)5/h9-10,17,20,22-25,27-28H,7-8,11-15H2,1-6H3/t17-,20-,22+,23-,24-,25+,27+,28+,30+,31-,32+/m0/s1

Standard InChI Key:  KKWMXUXYPBDQQX-QJOQXPENSA-N

Alternative Forms

1. Parent:

   

   ALA3234488

   [(2R)-2-[(1S)-1-[(1S,2R,6R,7S,9R,11S,12S,15R,16S)-6-acetyloxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-15-yl]ethyl]-4-methyl-6-oxo-2,3-dihydropyran-5-yl]methyl acetate

Molecule Features

Natural Product: No

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: 554.68

Molecular Weight (Monoisotopic): 554.2880

AlogP: 4.49

#Rotatable Bonds: 5

Polar Surface Area: 108.50

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.53

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 4.46

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.28

Np Likeness Score: 3.41

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. Xu YM, Brooks AD, Wijeratne EM, Henrich CJ, Tewary P, Sayers TJ, Gunatilaka AA..  (2017)  17β-Hydroxywithanolides as Sensitizers of Renal Carcinoma Cells to Tumor Necrosis Factor-α Related Apoptosis Inducing Ligand (TRAIL) Mediated Apoptosis: Structure-Activity Relationships.,  60  (7): [PMID:28257574] [10.1021/acs.jmedchem.7b00069]

3. 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