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

ID: ALA4063112

PubChem CID: 130472269

Max Phase: Preclinical

Molecular Formula: C26H24N4O3

Molecular Weight: 440.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1N1C(=O)c3cccc4c(N5CCCC5)ccc(c34)C1=O)n(C)c(=O)n2C

Standard InChI:  InChI=1S/C26H24N4O3/c1-15-13-21-22(28(3)26(33)27(21)2)14-20(15)30-24(31)17-8-6-7-16-19(29-11-4-5-12-29)10-9-18(23(16)17)25(30)32/h6-10,13-14H,4-5,11-12H2,1-3H3

Standard InChI Key:  JBAYIFKKENLJOW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.7112   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1385   -2.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4231   -1.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7101   -3.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9973   -3.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9980   -4.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7175   -4.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4249   -3.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4250   -4.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1295   -4.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8383   -4.4705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8382   -3.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1293   -3.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5487   -4.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5464   -5.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2595   -6.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.7683   -5.9626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2518   -5.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7608   -4.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5531   -3.2407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1284   -5.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0114   -3.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0275   -6.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0769   -5.2847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8309   -6.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2824   -3.2406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1969   -2.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3897   -2.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9779   -2.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5307   -3.5800    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
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 15 16  1  0
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 18 17  2  0
 17 14  1  0
 11 14  1  0
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 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 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063112

   ---

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: 440.50

Molecular Weight (Monoisotopic): 440.1848

AlogP: 3.74

#Rotatable Bonds: 2

Polar Surface Area: 67.55

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.31

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -1.03

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