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

ID: ALA4171143

PubChem CID: 984803

Max Phase: Preclinical

Molecular Formula: C18H18N2O5S

Molecular Weight: 374.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18N2O5S/c1-2-19-13-8-9-15(11-5-3-6-12(16(11)13)17(19)21)26(24,25)20-10-4-7-14(20)18(22)23/h3,5-6,8-9,14H,2,4,7,10H2,1H3,(H,22,23)/t14-/m1/s1

Standard InChI Key:  GWXPEKYEANOENV-CQSZACIVSA-N

Molfile:  

     RDKit          2D

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    6.4509  -20.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4550  -21.0324    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1606  -20.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160  -23.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2345  -23.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389  -22.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2315  -21.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6409  -21.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377  -20.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210  -20.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153  -21.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098  -22.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4154  -21.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175  -21.3398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159  -22.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551  -22.6565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424  -20.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8631  -21.7452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748  -20.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309  -22.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1393  -23.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8522  -22.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6842  -21.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2321  -21.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0311  -21.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9810  -20.4477    0.0000 O   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
 13  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 13  2  0
 12 13  1  0
 14 15  1  0
 15 12  1  0
 14 11  1  0
 15 16  2  0
 14 17  1  0
  8  2  1  0
  2 18  1  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
 23 24  1  1
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171143

   (2R)-1-(1-ethyl-2-oxobenzo[cd]indol-6-yl)sulfonylpyrrolidine-2-carboxylic acid

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: 374.42

Molecular Weight (Monoisotopic): 374.0936

AlogP: 2.06

#Rotatable Bonds: 4

Polar Surface Area: 94.99

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.02

CX Basic pKa: ┄

CX LogP: 1.45

CX LogD: -2.02

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.88

Np Likeness Score: -1.39

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