4-((2-Bromo-4-(3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-9-yl)phenoxy)methyl)benzoic acid

ID: ALA4171987

PubChem CID: 3333810

Max Phase: Preclinical

Molecular Formula: C31H32BrNO5

Molecular Weight: 578.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC(=O)C2=C(C1)NC1=C(C(=O)CC(C)(C)C1)C2c1ccc(OCc2ccc(C(=O)O)cc2)c(Br)c1

Standard InChI:  InChI=1S/C31H32BrNO5/c1-30(2)12-21-27(23(34)14-30)26(28-22(33-21)13-31(3,4)15-24(28)35)19-9-10-25(20(32)11-19)38-16-17-5-7-18(8-6-17)29(36)37/h5-11,26,33H,12-16H2,1-4H3,(H,36,37)

Standard InChI Key:  GGYQEXHKGCVHOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.1834   -6.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8915   -6.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6011   -6.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5983   -5.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8897   -4.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4754   -6.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7680   -6.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4748   -7.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3045   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0137   -5.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7199   -4.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4276   -5.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1332   -4.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1306   -4.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4164   -3.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7136   -4.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8362   -3.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2463   -2.9134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8270   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5373   -2.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5400   -1.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8340   -1.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1237   -1.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1193   -2.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2462   -3.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5424   -4.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5437   -4.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2473   -5.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9511   -4.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9514   -4.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8361   -5.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4109   -2.9168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4286   -6.1923    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.4193   -0.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2365   -0.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7665   -4.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3538   -5.6502    0.0000 C   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
  2  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 27  1  0
 18 20  1  0
 26 19  1  0
 19 21  1  0
 20 21  2  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 26 27  2  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 28 32  2  0
 25 33  2  0
 13 34  1  0
 23 35  1  0
 23 36  1  0
 30 37  1  0
 30 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171987

   4-[[2-Bromo-4-(3,3,6,6-tetramethyl-1,8-dioxo-2,4,5,7,9,10-hexahydroacridin-9-yl)phenoxy]methyl]benzoic acid

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: 578.50

Molecular Weight (Monoisotopic): 577.1464

AlogP: 6.70

#Rotatable Bonds: 5

Polar Surface Area: 92.70

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 5.57

CX LogD: 2.45

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.41

Np Likeness Score: -0.44

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]

Source

Source(1):

• Scientific Literature