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

ID: ALA4062266

PubChem CID: 130471730

Max Phase: Preclinical

Molecular Formula: C25H24N4O3

Molecular Weight: 428.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNc1ccc2c3c(cccc13)C(=O)N(c1cc3c(cc1C)n(C)c(=O)n3C)C2=O

Standard InChI:  InChI=1S/C25H24N4O3/c1-5-11-26-18-10-9-17-22-15(18)7-6-8-16(22)23(30)29(24(17)31)19-13-21-20(12-14(19)2)27(3)25(32)28(21)4/h6-10,12-13,26H,5,11H2,1-4H3

Standard InChI Key:  NMRMIPFJPBQHHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   17.0361  -10.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4634  -10.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7479   -9.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0350  -10.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3221  -11.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3228  -12.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0424  -12.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7497  -11.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7498  -12.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4543  -12.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -12.0955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -11.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4541  -10.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8736  -12.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8712  -13.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5843  -13.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5850  -12.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2987  -12.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3033  -13.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0931  -13.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5766  -12.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0857  -12.2463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8779  -10.8658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4532  -13.3273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3362  -11.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3524  -14.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4016  -12.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1557  -13.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6072  -10.8656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1845  -10.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1833  -10.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8986  -11.2786    0.0000 C   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
  5 29  1  0
 29 32  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4062266

   ---

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: 428.49

Molecular Weight (Monoisotopic): 428.1848

AlogP: 3.96

#Rotatable Bonds: 4

Polar Surface Area: 76.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.04

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -1.14

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