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

ID: ALA4080780

PubChem CID: 130471695

Max Phase: Preclinical

Molecular Formula: C22H17N3O4

Molecular Weight: 387.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1N1C(=O)c3cccc4cccc(c34)C1=O)n(C)c(=O)n2C

Standard InChI:  InChI=1S/C22H17N3O4/c1-23-15-10-17(18(29-3)11-16(15)24(2)22(23)28)25-20(26)13-8-4-6-12-7-5-9-14(19(12)13)21(25)27/h4-11H,1-3H3

Standard InChI Key:  DWEBZJMPQVJZAL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   24.3366  -10.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3374  -11.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0585  -11.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.1090  -11.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8966  -10.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4685  -12.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3587  -10.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3748  -13.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4246  -12.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1728  -13.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1710  -13.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4080780

   ---

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: 387.40

Molecular Weight (Monoisotopic): 387.1219

AlogP: 2.84

#Rotatable Bonds: 2

Polar Surface Area: 73.54

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -0.75

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