2-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

ID: ALA4077619

PubChem CID: 4102773

Max Phase: Preclinical

Molecular Formula: C21H15N3O3

Molecular Weight: 357.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)n(C)c2cc(N3C(=O)c4cccc5cccc(c45)C3=O)ccc21

Standard InChI:  InChI=1S/C21H15N3O3/c1-22-16-10-9-13(11-17(16)23(2)21(22)27)24-19(25)14-7-3-5-12-6-4-8-15(18(12)14)20(24)26/h3-11H,1-2H3

Standard InChI Key:  PKAHAABFUSYZKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.4932  -17.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7805  -17.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0742  -18.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3640  -19.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3647  -19.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0816  -20.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7822  -19.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7823  -19.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4842  -20.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1905  -19.9548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1904  -19.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4841  -18.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8984  -20.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8960  -21.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6065  -21.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6072  -19.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3182  -20.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3228  -21.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1092  -21.4410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5882  -20.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1019  -20.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9026  -18.7325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4832  -21.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3500  -19.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3661  -22.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4095  -20.7653    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4077619

   2-(1,3-Dimethyl-2-oxobenzimidazol-5-yl)benzo[de]isoquinoline-1,3-dione

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: 357.37

Molecular Weight (Monoisotopic): 357.1113

AlogP: 2.83

#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: 2.83

CX LogD: 2.83

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.49

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