5,1'-dimethoxy-7,3'-dimethyl-[2,2']binaphthalenyl-1,4,5',8'-tetraone

ID: ALA242992

Chembl Id: CHEMBL242992

Cas Number: 39093-14-6

PubChem CID: 10341035

Max Phase: Preclinical

Molecular Formula: C24H18O6

Molecular Weight: 402.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)cc2c1C(=O)C=C(c1c(C)cc3c(c1OC)C(=O)C=CC3=O)C2=O

Standard InChI:  InChI=1S/C24H18O6/c1-11-7-14-21(19(8-11)29-3)18(27)10-15(23(14)28)20-12(2)9-13-16(25)5-6-17(26)22(13)24(20)30-4/h5-10H,1-4H3

Standard InChI Key:  PEHFVNNNUFIZPR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA242992

   Diospyrin, dimethyl ether

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: 402.40

Molecular Weight (Monoisotopic): 402.1103

AlogP: 3.72

#Rotatable Bonds: 3

Polar Surface Area: 86.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.39

CX LogD: 3.39

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.78

Np Likeness Score: 1.10

References

1. Das Sarma M, Ghosh R, Patra A, Hazra B..  (2007)  Synthesis and antiproliferative activity of some novel derivatives of diospyrin, a plant-derived naphthoquinonoid.,  15  (11): [PMID:17400463] [10.1016/j.bmc.2007.03.050]

2. Das Sarma M, Ghosh R, Patra A, Hazra B..  (2008)  Synthesis of novel aminoquinonoid analogues of diospyrin and evaluation of their inhibitory activity against murine and human cancer cells.,  43  (9): [PMID:18281125] [10.1016/j.ejmech.2007.11.028]

3. Sagar S, Kaur M, Minneman KP, Bajic VB..  (2010)  Anti-cancer activities of diospyrin, its derivatives and analogues.,  45  (9): [PMID:20615584] [10.1016/j.ejmech.2010.06.021]

4. Pullella GA,Vuong D,Lacey E,Piggott MJ.  (2020)  Total Synthesis of the Antitumor-Antitubercular 2,6'-Bijuglone Natural Product Diospyrin and Its 3,6'-Isomer.,  83  (12.0): [PMID:33314932] [10.1021/acs.jnatprod.0c00800]

Source

Source(1):

• Scientific Literature