Acetic acid 10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-20-oxa-cyclopropa[14,15]cyclopenta[a]phenanthren-3-yl ester

ID: ALA401421

Chembl Id: CHEMBL401421

PubChem CID: 44444259

Max Phase: Preclinical

Molecular Formula: C26H34O5

Molecular Weight: 426.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Resibufogenin-3-Acetate | Resibufogenin-3-Acetate|CHEMBL401421|SCHEMBL10589905

Canonical SMILES:  CC(=O)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](c4ccc(=O)oc4)C[C@H]4O[C@]342)C1

Standard InChI:  InChI=1S/C26H34O5/c1-15(27)30-18-8-10-24(2)17(12-18)5-6-20-19(24)9-11-25(3)21(13-22-26(20,25)31-22)16-4-7-23(28)29-14-16/h4,7,14,17-22H,5-6,8-13H2,1-3H3/t17-,18+,19+,20-,21-,22-,24+,25-,26-/m1/s1

Standard InChI Key:  PYQLJWZNYPKLBI-AHBNOPRMSA-N

Alternative Forms

1. Parent:

   

   ALA401421

   Resibufogenin-3-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: 426.55

Molecular Weight (Monoisotopic): 426.2406

AlogP: 4.83

#Rotatable Bonds: 2

Polar Surface Area: 69.04

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: 2.96

References

1. Kamano Y, Yamashita A, Nogawa T, Morita H, Takeya K, Itokawa H, Segawa T, Yukita A, Saito K, Katsuyama M, Pettit GR..  (2002)  QSAR evaluation of the Ch'an Su and related bufadienolides against the colchicine-resistant primary liver carcinoma cell line PLC/PRF/5(1).,  45  (25): [PMID:12459012] [10.1021/jm0202066]

2. Zhang J, Sun Y, Liu JH, Yu BY, Xu Q..  (2007)  Microbial transformation of three bufadienolides by Nocardia sp. and some insight for the cytotoxic structure-activity relationship (SAR).,  17  (22): [PMID:17911017] [10.1016/j.bmcl.2007.09.065]

3. Enomoto A, Rho MC, Komiyama K, Hayashi M..  (2004)  Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells.,  67  (12): [PMID:15620253] [10.1021/np049950e]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays