rac-6-(Piperidin-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: ALA4092917

PubChem CID: 130471733

Max Phase: Preclinical

Molecular Formula: C27H26N4O3

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1N1C(=O)c3cccc4c(N5CCCCC5)ccc(c34)C1=O)n(C)c(=O)n2C

Standard InChI:  InChI=1S/C27H26N4O3/c1-16-14-22-23(29(3)27(34)28(22)2)15-21(16)31-25(32)18-9-7-8-17-20(30-12-5-4-6-13-30)11-10-19(24(17)18)26(31)33/h7-11,14-15H,4-6,12-13H2,1-3H3

Standard InChI Key:  AHCZNZBUHSRPCU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.9469  -16.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8853  -19.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6393  -20.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906  -17.5119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092917

   ---

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: 454.53

Molecular Weight (Monoisotopic): 454.2005

AlogP: 4.13

#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: 3.76

CX LogP: 4.30

CX LogD: 4.30

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -1.01

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