9-(3-Bromo-4-((3-fluorobenzyl)oxy)phenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

ID: ALA4173961

PubChem CID: 1232088

Max Phase: Preclinical

Molecular Formula: C26H23BrFNO3

Molecular Weight: 496.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCCC2=C1C(c1ccc(OCc3cccc(F)c3)c(Br)c1)C1=C(CCCC1=O)N2

Standard InChI:  InChI=1S/C26H23BrFNO3/c27-18-13-16(10-11-23(18)32-14-15-4-1-5-17(28)12-15)24-25-19(6-2-8-21(25)30)29-20-7-3-9-22(31)26(20)24/h1,4-5,10-13,24,29H,2-3,6-9,14H2

Standard InChI Key:  LBGBZNIPLODINR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    0.5558  -28.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546  -29.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2627  -29.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9723  -29.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695  -28.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609  -27.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6757  -27.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849  -28.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0911  -27.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987  -28.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5044  -27.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018  -27.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7876  -26.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0848  -27.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2074  -26.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6175  -25.8113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1981  -25.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084  -25.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9111  -24.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2052  -24.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949  -24.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4905  -25.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820  -25.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7998  -29.0902    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.6156  -26.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9135  -27.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9196  -27.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6261  -28.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3281  -27.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3237  -27.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2144  -28.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625  -30.3296    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 26  1  0
 15 17  1  0
 25 16  1  0
 16 18  1  0
 17 18  2  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 10 24  1  0
 25 26  2  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  2  0
  3 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173961

   9-[3-Bromo-4-[(3-fluorophenyl)methoxy]phenyl]-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione

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: 496.38

Molecular Weight (Monoisotopic): 495.0845

AlogP: 5.87

#Rotatable Bonds: 4

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.88

CX LogD: 4.88

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -0.99

References

1. Xiong H, Han J, Wang J, Lu W, Wang C, Chen Y, Fulin Lian, Zhang N, Liu YC, Zhang C, Ding H, Jiang H, Lu W, Luo C, Zhou B..  (2018)  Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening.,  151  [PMID:29665527] [10.1016/j.ejmech.2018.02.005]

2. Joubert J, Kapp E..  (2020)  Discovery of 9-phenylacridinediones as highly selective butyrylcholinesterase inhibitors through structure-based virtual screening.,  30  (9): [PMID:32165042] [10.1016/j.bmcl.2020.127075]

Source

Source(1):

• Scientific Literature