rac-6-(4-Hydroxybutyl)-2-(1,3,6-trimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

ID: ALA4059651

PubChem CID: 130471876

Max Phase: Preclinical

Molecular Formula: C26H25N3O4

Molecular Weight: 443.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H25N3O4/c1-15-13-21-22(28(3)26(33)27(21)2)14-20(15)29-24(31)18-9-6-8-17-16(7-4-5-12-30)10-11-19(23(17)18)25(29)32/h6,8-11,13-14,30H,4-5,7,12H2,1-3H3

Standard InChI Key:  LGZFUXSDGGGPHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   30.7697  -18.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1970  -18.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4816  -17.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7685  -19.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0557  -19.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0565  -20.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7760  -20.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4834  -19.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4834  -20.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1879  -20.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8968  -20.3457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8967  -19.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1878  -19.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6072  -20.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6048  -21.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3180  -21.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3187  -20.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0323  -20.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0370  -21.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8268  -21.8378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3103  -21.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8193  -20.4966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6116  -19.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1869  -21.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0699  -19.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0860  -22.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1354  -21.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8894  -21.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3408  -19.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3400  -18.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6251  -17.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6244  -17.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9094  -16.6421    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
 15 28  1  0
  5 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4059651

   ---

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: 443.50

Molecular Weight (Monoisotopic): 443.1845

AlogP: 3.45

#Rotatable Bonds: 5

Polar Surface Area: 84.54

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -0.50

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