4-cyano-N-(1,3-diethyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-methoxybenzenesulfonamide

ID: ALA4067917

PubChem CID: 137632687

Max Phase: Preclinical

Molecular Formula: C21H21N3O4S

Molecular Weight: 411.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc2cc(NS(=O)(=O)c3ccc(C#N)cc3OC)ccc2n(CC)c1=O

Standard InChI:  InChI=1S/C21H21N3O4S/c1-4-15-11-16-12-17(7-8-18(16)24(5-2)21(15)25)23-29(26,27)20-9-6-14(13-22)10-19(20)28-3/h6-12,23H,4-5H2,1-3H3

Standard InChI Key:  GKWMKPPUPBLQAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.8730  -15.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4686  -14.7672    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0596  -15.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1826  -14.3545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8952  -14.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8940  -15.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6062  -15.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6044  -14.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3172  -14.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3160  -15.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0263  -15.9974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7382  -15.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7394  -14.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0286  -14.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4489  -16.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0240  -16.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596  -14.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7590  -13.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582  -13.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458  -13.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3428  -14.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481  -14.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6406  -13.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355  -12.7047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4489  -14.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1548  -14.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7306  -17.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446  -15.5842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3351  -15.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 11 16  1  0
  5  4  1  0
  4  2  1  0
  2 17  1  0
 17 18  1  0
 17 22  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 20 23  1  0
 23 24  3  0
 13 25  1  0
 25 26  1  0
 16 27  1  0
 22 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067917

   ---

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: 411.48

Molecular Weight (Monoisotopic): 411.1253

AlogP: 3.26

#Rotatable Bonds: 6

Polar Surface Area: 101.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.99

CX Basic pKa: ┄

CX LogP: 2.84

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.85

References

1. Igoe N, Bayle ED, Tallant C, Fedorov O, Meier JC, Savitsky P, Rogers C, Morias Y, Scholze S, Boyd H, Cunoosamy D, Andrews DM, Cheasty A, Brennan PE, Müller S, Knapp S, Fish PV..  (2017)  Design of a Chemical Probe for the Bromodomain and Plant Homeodomain Finger-Containing (BRPF) Family of Proteins.,  60  (16): [PMID:28714688] [10.1021/acs.jmedchem.7b00611]

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