27-acetoxy-5beta,6beta-epoxy-4beta-hydroxy-1-oxo-witha-2,24-dienolide

ID: ALA2047407

Chembl Id: CHEMBL2047407

PubChem CID: 57328756

Max Phase: Preclinical

Molecular Formula: C30H40O7

Molecular Weight: 512.64

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](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)OC1=O

Standard InChI:  InChI=1S/C30H40O7/c1-15-12-23(36-27(34)19(15)14-35-17(3)31)16(2)20-6-7-21-18-13-26-30(37-26)25(33)9-8-24(32)29(30,5)22(18)10-11-28(20,21)4/h8-9,16,18,20-23,25-26,33H,6-7,10-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,25-,26+,28+,29-,30+/m0/s1

Standard InChI Key:  ARTYOOFBEGPUAU-NSXHFEBNSA-N

Alternative Forms

1. Parent:

   

   ALA2047407

   27-O-acetyl-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: 512.64

Molecular Weight (Monoisotopic): 512.2774

AlogP: 3.92

#Rotatable Bonds: 4

Polar Surface Area: 102.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.46

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 4.02

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.45

Np Likeness Score: 3.60

References

1. Llanos GG, Araujo LM, Jiménez IA, Moujir LM, Bazzocchi IL..  (2012)  Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.,  54  [PMID:22705001] [10.1016/j.ejmech.2012.05.032]

2. 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]

3. Llanos GG, Araujo LM, Jiménez IA, Moujir LM, Rodríguez J, Jiménez C, Bazzocchi IL..  (2017)  Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.,  140  [PMID:28923386] [10.1016/j.ejmech.2017.09.004]

4. Huryn DM, Kornfilt DJP, Wipf P..  (2020)  p97: An Emerging Target for Cancer, Neurodegenerative Diseases, and Viral Infections.,  63  (5): [PMID:31550150] [10.1021/acs.jmedchem.9b01318]

5. Freitas Misakyan MF, Wijeratne EMK, Issa ME, Xu YM, Monteillier A, Gunatilaka AAL, Cuendet M..  (2021)  Structure-Activity Relationships of Withanolides as Antiproliferative Agents for Multiple Myeloma: Comparison of Activity in 2D Models and a 3D Coculture Model.,  84  (8.0): [PMID:34445874] [10.1021/acs.jnatprod.1c00446]

Source

Source(1):

• Scientific Literature