ID: ALA1269107

Max Phase: Preclinical

Molecular Formula: C36H26O8

Molecular Weight: 586.60

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1=C(C2=C(C)C(=O)c3c(cc(O)c(O)c3Cc3ccccc3)C2=O)C(=O)c2cc(O)c(O)c(Cc3ccccc3)c2C1=O

Standard InChI:  InChI=1S/C36H26O8/c1-17-27(35(43)23-15-25(37)33(41)21(29(23)31(17)39)13-19-9-5-3-6-10-19)28-18(2)32(40)30-22(14-20-11-7-4-8-12-20)34(42)26(38)16-24(30)36(28)44/h3-12,15-16,37-38,41-42H,13-14H2,1-2H3

Standard InChI Key:  IEJPMWKHSOLTHK-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: 586.60

Molecular Weight (Monoisotopic): 586.1628

AlogP: 5.78

#Rotatable Bonds: 5

Polar Surface Area: 149.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.60

CX Basic pKa:

CX LogP: 6.19

CX LogD: 4.97

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.22

Np Likeness Score: 0.64

References

1. Wei J, Kitada S, Stebbins JL, Placzek W, Zhai D, Wu B, Rega MF, Zhang Z, Cellitti J, Yang L, Dahl R, Reed JC, Pellecchia M..  (2010)  Synthesis and biological evaluation of Apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.,  53  (22): [PMID:21033669] [10.1021/jm100746q]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

3.  (2015)  Apogossypolone derivatives as anticancer agents, 

4. Yap JL, Chen L, Lanning ME, Fletcher S..  (2017)  Expanding the Cancer Arsenal with Targeted Therapies: Disarmament of the Antiapoptotic Bcl-2 Proteins by Small Molecules.,  60  (3): [PMID:27749061] [10.1021/acs.jmedchem.5b01888]

5. 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]

6. Negi A, Murphy PV..  (2021)  Development of Mcl-1 inhibitors for cancer therapy.,  210  [PMID:33333396] [10.1016/j.ejmech.2020.113038]

7. Li X, Dou J, You Q, Jiang Z..  (2021)  Inhibitors of BCL2A1/Bfl-1 protein: Potential stock in cancer therapy.,  220  [PMID:34034128] [10.1016/j.ejmech.2021.113539]

Source

Source(3):

• Scientific Literature
• AstraZeneca Deposited Data
• BindingDB Database