(1S,6R)-6-((3S,5R,8R,9S,10S,13R,17S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[14,15]cyclopenta[a]phenanthren-17-yl)-2,7-dioxa-bicyclo[4.1.0]hept-4-en-3-one

ID: ALA521034

Chembl Id: CHEMBL521034

PubChem CID: 10092398

Max Phase: Preclinical

Molecular Formula: C24H32O5

Molecular Weight: 400.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 20R,21-Epoxyresibufogenin | 20R,21-Epoxyresibufogenin|CHEMBL521034

Canonical SMILES:  C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@]34C=CC(=O)O[C@H]3O4)C[C@H]3O[C@]132

Standard InChI:  InChI=1S/C24H32O5/c1-21-8-5-14(25)11-13(21)3-4-16-15(21)6-9-22(2)17(12-18-24(16,22)28-18)23-10-7-19(26)27-20(23)29-23/h7,10,13-18,20,25H,3-6,8-9,11-12H2,1-2H3/t13-,14+,15+,16-,17+,18-,20+,21+,22-,23-,24-/m1/s1

Standard InChI Key:  JZDMFDWKCWMAMI-LXXIVLROSA-N

Alternative Forms

1. Parent:

   

   ALA521034

   20R,21-Epoxyresibufogenin

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: 400.52

Molecular Weight (Monoisotopic): 400.2250

AlogP: 3.35

#Rotatable Bonds: 1

Polar Surface Area: 71.59

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: 3.68

References

1. 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]

2. Kamano Y, Nogawa T, Yamashita A, Hayashi M, Inoue M, Drasar P, Pettit GR..  (2002)  Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su".,  65  (7): [PMID:12141860] [10.1021/np0200360]

Source

Source(1):

• Scientific Literature