(R)-1-(1-ethyl-2-oxo-1,2-dihydrobenzo[cd]indol-6-ylsulfonyl)pyrrolidine-2-carbohydrazide

ID: ALA4175673

PubChem CID: 145971920

Max Phase: Preclinical

Molecular Formula: C18H20N4O4S

Molecular Weight: 388.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)c2cccc3c(S(=O)(=O)N4CCC[C@@H]4C(=O)NN)ccc1c23

Standard InChI:  InChI=1S/C18H20N4O4S/c1-2-21-13-8-9-15(11-5-3-6-12(16(11)13)18(21)24)27(25,26)22-10-4-7-14(22)17(23)20-19/h3,5-6,8-9,14H,2,4,7,10,19H2,1H3,(H,20,23)/t14-/m1/s1

Standard InChI Key:  IVNSVSHWDOSFSB-CQSZACIVSA-N

Molfile:  

     RDKit          2D

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   36.9139  -20.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9181  -21.0035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.6237  -20.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8790  -23.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6976  -23.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1020  -22.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6946  -21.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1040  -21.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7008  -20.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8841  -20.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4784  -20.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4729  -22.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8785  -21.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6806  -21.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6790  -22.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0181  -22.6276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0055  -20.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3262  -21.7163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9947  -22.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5992  -23.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3090  -22.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1430  -21.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0378  -20.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6917  -21.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4905  -21.3704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4417  -20.4199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0393  -20.7648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
 12  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  7  8  2  0
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  9 10  2  0
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 12 13  1  0
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 15 12  1  0
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 15 16  2  0
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  8  2  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 17 23  1  0
 22 24  1  1
 24 25  1  0
 24 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175673

   ---

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: 388.45

Molecular Weight (Monoisotopic): 388.1205

AlogP: 0.96

#Rotatable Bonds: 4

Polar Surface Area: 112.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.67

CX Basic pKa: 2.83

CX LogP: 0.35

CX LogD: 0.35

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: -1.73

References

1. Feng Y, Xiao S, Chen Y, Jiang H, Liu N, Luo C, Chen S, Chen H..  (2018)  Design, synthesis and biological evaluation of benzo[cd]indol-2(1H)-ones derivatives as BRD4 inhibitors.,  152  [PMID:29730189] [10.1016/j.ejmech.2018.04.048]

Source

Source(1):

• Scientific Literature