ID: ALA463065

Max Phase: Preclinical

Molecular Formula: C24H34O5

Molecular Weight: 402.53

Molecule Type: Small molecule

Representations

Synonyms (1): Desacetylbufotalin
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)[C@@H](O)C[C@]12O

Standard InChI:  InChI=1S/C24H34O5/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)21(19(26)12-24(18,23)28)14-3-6-20(27)29-13-14/h3,6,13,15-19,21,25-26,28H,4-5,7-12H2,1-2H3/t15-,16+,17+,18-,19+,21+,22+,23-,24+/m1/s1

Standard InChI Key:  MWFCMSURKYLINK-QDLCSJEJSA-N

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

Properties

Molecular Weight: 402.53

Molecular Weight (Monoisotopic): 402.2406

AlogP: 3.21

#Rotatable Bonds: 1

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.99

CX Basic pKa:

CX LogP: 1.90

CX LogD: 1.90

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: 2.80

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. Nogawa T, Kamano Y, Yamashita A, Pettit GR..  (2001)  Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.,  64  (9): [PMID:11575946] [10.1021/np0101088]

3. Liu J, Zhang D, Li Y, Chen W, Ruan Z, Deng L, Wang L, Tian H, Yiu A, Fan C, Luo H, Liu S, Wang Y, Xiao G, Chen L, Ye W..  (2013)  Discovery of bufadienolides as a novel class of ClC-3 chloride channel activators with antitumor activities.,  56  (14): [PMID:23799775] [10.1021/jm400881m]

Source

Source(1):

• Scientific Literature