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

ID: ALA4067538

PubChem CID: 130472274

Max Phase: Preclinical

Molecular Formula: C23H19N3O4

Molecular Weight: 401.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)[nH]c2cc(N3C(=O)c4cccc5c(CCCO)ccc(c45)C3=O)ccc21

Standard InChI:  InChI=1S/C23H19N3O4/c1-25-19-10-8-14(12-18(19)24-23(25)30)26-21(28)16-6-2-5-15-13(4-3-11-27)7-9-17(20(15)16)22(26)29/h2,5-10,12,27H,3-4,11H2,1H3,(H,24,30)

Standard InChI Key:  OGFBLTYSHLJDTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.6706   -3.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0843   -3.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3757   -2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -4.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -4.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641   -5.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6768   -5.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775   -4.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -5.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0754   -5.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7775   -5.3444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7774   -4.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752   -4.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813   -5.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4789   -6.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1852   -6.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1859   -5.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8929   -5.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6797   -6.8224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1587   -6.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6724   -5.4939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -4.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743   -6.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9365   -7.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9759   -6.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2553   -4.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545   -3.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5464   -2.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456   -2.0838    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
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  8  9  1  0
  8 13  2  0
  9 10  1  0
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 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
 20 25  1  0
 21 26  2  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067538

   ---

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: 401.42

Molecular Weight (Monoisotopic): 401.1376

AlogP: 2.75

#Rotatable Bonds: 4

Polar Surface Area: 95.40

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.78

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -0.58

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]

2. Palmer, Wylie S WS and 21 more authors.  2016-02-25  Structure-Guided Design of IACS-9571, a Selective High-Affinity Dual TRIM24-BRPF1 Bromodomain Inhibitor.  [PMID:26061247]

3. Romero, F Anthony FA and 5 more authors.  2016-02-25  Disrupting Acetyl-Lysine Recognition: Progress in the Development of Bromodomain Inhibitors.  [PMID:26572217]

4. Moustakim, Moses; Clark, Peter G K; Hay, Duncan A; Dixon, Darren J and Brennan, Paul E.  2016-12-07  Chemical probes and inhibitors of bromodomains outside the BET family.  [PMID:29170712]

Source

Source(1):

• Scientific Literature