5-(4-ethoxyphenylsulfonamido)-1-(4-ethoxyphenylsulfonyl)-N-hydroxy-2-methyl-1H-benzo[g]indole-3-carboxamide

ID: ALA4077198

PubChem CID: 137650952

Max Phase: Preclinical

Molecular Formula: C30H29N3O8S2

Molecular Weight: 623.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(S(=O)(=O)Nc2cc3c(C(=O)NO)c(C)n(S(=O)(=O)c4ccc(OCC)cc4)c3c3ccccc23)cc1

Standard InChI:  InChI=1S/C30H29N3O8S2/c1-4-40-20-10-14-22(15-11-20)42(36,37)32-27-18-26-28(30(34)31-35)19(3)33(29(26)25-9-7-6-8-24(25)27)43(38,39)23-16-12-21(13-17-23)41-5-2/h6-18,32,35H,4-5H2,1-3H3,(H,31,34)

Standard InChI Key:  KBWJOQJHXVYEPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 47  0  0  0  0  0  0  0  0999 V2000
    1.8449   -8.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373   -8.3205    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588   -7.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5317   -4.0488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7145   -4.0488    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231   -4.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983   -5.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972   -6.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6052   -6.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -5.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3121   -5.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128   -6.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -5.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0158   -5.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7296   -6.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -6.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878   -7.7157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -7.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364   -7.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -4.4645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4222   -2.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183   -2.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079   -1.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -2.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0075   -2.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -0.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9931   -0.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -0.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085   -8.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362   -6.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6815   -7.4972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907   -6.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4812   -7.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900   -9.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -9.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902  -10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898  -10.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9391  -10.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862   -9.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402  -11.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393  -11.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909  -12.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  2  0
  6  5  2  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 12 16  1  0
 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 14 20  1  0
 20  5  1  0
  5 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  1  0
 24 27  1  0
 28 29  1  0
 18 30  1  0
 19 31  1  0
 31 32  1  0
 31 33  2  0
 32 34  1  0
 17  2  1  0
  2 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
 41 42  1  0
 38 41  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4077198

   ---

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: 623.71

Molecular Weight (Monoisotopic): 623.1396

AlogP: 5.06

#Rotatable Bonds: 10

Polar Surface Area: 153.03

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.65

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.75

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.14

Np Likeness Score: -1.01

References

1. Yasuda D, Yuasa A, Obata R, Nakajima M, Takahashi K, Ohe T, Ichimura Y, Komatsu M, Yamamoto M, Imamura R, Kojima H, Okabe T, Nagano T, Mashino T..  (2017)  Discovery of benzo[g]indoles as a novel class of non-covalent Keap1-Nrf2 protein-protein interaction inhibitor.,  27  (22): [PMID:29037947] [10.1016/j.bmcl.2017.10.008]

2. Tran KT, Pallesen JS, Solbak SMØ, Narayanan D, Baig A, Zang J, Aguayo-Orozco A, Carmona RMC, Garcia AD, Bach A..  (2019)  A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity.,  62  (17): [PMID:31411465] [10.1021/acs.jmedchem.9b00723]

Source

Source(1):

• Scientific Literature