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

ID: ALA4099171

PubChem CID: 130471777

Max Phase: Preclinical

Molecular Formula: C23H16N4O3

Molecular Weight: 396.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H16N4O3/c1-12-7-18-19(26(3)23(30)25(18)2)10-17(12)27-21(28)15-6-4-5-14-8-13(11-24)9-16(20(14)15)22(27)29/h4-10H,1-3H3

Standard InChI Key:  KZNDNGJCFUTVMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   24.8798  -18.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1637  -17.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4500  -18.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7365  -19.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7372  -20.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4574  -20.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1655  -19.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1656  -20.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8707  -20.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5803  -20.0905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5802  -19.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8706  -18.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2915  -20.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2891  -21.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0029  -21.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0036  -20.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7180  -20.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7226  -21.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5132  -21.5842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9973  -20.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5057  -20.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2958  -18.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8697  -21.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7565  -19.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7727  -22.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8231  -20.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5730  -21.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0246  -20.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3105  -20.9272    0.0000 N   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
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  8  9  1  0
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  9 10  1  0
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 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
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 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
 29 30  3  0
  6 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099171

   ---

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: 396.41

Molecular Weight (Monoisotopic): 396.1222

AlogP: 3.01

#Rotatable Bonds: 1

Polar Surface Area: 88.10

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -1.09

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