rac-5-Bromo-2-(1,3,6-trimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

ID: ALA4081145

PubChem CID: 130471696

Max Phase: Preclinical

Molecular Formula: C22H16BrN3O3

Molecular Weight: 450.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1N1C(=O)c3cccc4cc(Br)cc(c34)C1=O)n(C)c(=O)n2C

Standard InChI:  InChI=1S/C22H16BrN3O3/c1-11-7-17-18(25(3)22(29)24(17)2)10-16(11)26-20(27)14-6-4-5-12-8-13(23)9-15(19(12)14)21(26)28/h4-10H,1-3H3

Standard InChI Key:  ZJQVEQKLMMZDON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
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   24.8272  -10.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1111   -9.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3975  -11.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6840  -11.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6848  -12.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4049  -12.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1130  -11.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1130  -12.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8181  -12.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5276  -12.2856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5275  -11.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8180  -11.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2387  -12.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2362  -13.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9500  -13.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9507  -12.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6650  -12.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6697  -13.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4602  -13.7790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9442  -13.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4527  -12.4366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2430  -11.0547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8171  -13.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7035  -11.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7196  -14.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7699  -13.1005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5202  -13.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9708  -12.7076    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0
 13  2  1  0
  2  3  2  0
  3  1  1  0
  8  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  9  2  0
  8  9  1  0
  8 13  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 11 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 12 23  2  0
 10 24  2  0
 22 25  1  0
 20 26  1  0
 21 27  2  0
 15 28  1  0
  6 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081145

   ---

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: 450.29

Molecular Weight (Monoisotopic): 449.0375

AlogP: 3.90

#Rotatable Bonds: 1

Polar Surface Area: 64.31

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -0.93

References

1. Bouché L, Christ CD, Siegel S, Fernández-Montalván AE, Holton SJ, Fedorov O, Ter Laak A, Sugawara T, Stöckigt D, Tallant C, Bennett J, Monteiro O, Díaz-Sáez L, Siejka P, Meier J, Pütter V, Weiske J, Müller S, Huber KVM, Hartung IV, Haendler B..  (2017)  Benzoisoquinolinediones as Potent and Selective Inhibitors of BRPF2 and TAF1/TAF1L Bromodomains.,  60  (9): [PMID:28402630] [10.1021/acs.jmedchem.7b00306]

Source

Source(1):

• Scientific Literature