ID: ALA551288

Max Phase: Preclinical

Molecular Formula: C28H30O6

Molecular Weight: 462.54

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc2c(C(C)C)c(O)c(O)cc2c(O)c1-c1c(C)cc2c(C(C)C)c(O)c(O)cc2c1O

Standard InChI:  InChI=1S/C28H30O6/c1-11(2)21-15-7-13(5)23(25(31)17(15)9-19(29)27(21)33)24-14(6)8-16-18(26(24)32)10-20(30)28(34)22(16)12(3)4/h7-12,29-34H,1-6H3

Standard InChI Key:  PBJKWGWHZVXBGU-UHFFFAOYSA-N

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

Properties

Molecular Weight: 462.54

Molecular Weight (Monoisotopic): 462.2042

AlogP: 6.76

#Rotatable Bonds: 3

Polar Surface Area: 121.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.68

CX Basic pKa:

CX LogP: 7.29

CX LogD: 7.27

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: 0.72

References

1. Wei J, Kitada S, Rega MF, Stebbins JL, Zhai D, Cellitti J, Yuan H, Emdadi A, Dahl R, Zhang Z, Yang L, Reed JC, Pellecchia M..  (2009)  Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.,  52  (14): [PMID:19555126] [10.1021/jm900472s]

2. Zhang L, Jiang H, Cao X, Zhao H, Wang F, Cui Y, Jiang B..  (2009)  Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.,  44  (10): [PMID:19447525] [10.1016/j.ejmech.2009.04.025]

3. Zhang L, Jiang H, Cao X, Zhao H, Wang F, Cui Y, Jiang B..  (2009)  Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling.,  44  (10): [PMID:19447525] [10.1016/j.ejmech.2009.04.025]

4.  (2015)  Naphthalene-based inhibitors of anti-apoptotic proteins, 

5. Nhu D, Lessene G, Huang DCS, Burns CJ.  (2016)  Small molecules targeting Mcl-1: the search for a silver bullet in cancer therapy,  7  (5): [10.1039/C5MD00582E]

6. Yang S, Mao Y, Zhang H, Xu Y, An J, Huang Z..  (2019)  The chemical biology of apoptosis: Revisited after 17 years.,  177  [PMID:31129454] [10.1016/j.ejmech.2019.05.019]

7. Gampe C, Verma VA..  (2020)  Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients.,  63  (23.0): [PMID:32916044] [10.1021/acs.jmedchem.0c01177]

8. Liu T, Wu Z, He Y, Xiao Y, Xia C..  (2020)  Single and dual target inhibitors based on Bcl-2: Promising anti-tumor agents for cancer therapy.,  201  [PMID:32563811] [10.1016/j.ejmech.2020.112446]

Source

Source(2):

• Scientific Literature
• BindingDB Database