(S)-2-(Benzofuran-3-yl)-N-(4-bromo-3-((3-methylpyrrolidin-1-yl)sulfonyl)phenyl)acetamide

ID: ALA4525009

PubChem CID: 155538742

Max Phase: Preclinical

Molecular Formula: C21H21BrN2O4S

Molecular Weight: 477.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1CCN(S(=O)(=O)c2cc(NC(=O)Cc3coc4ccccc34)ccc2Br)C1

Standard InChI:  InChI=1S/C21H21BrN2O4S/c1-14-8-9-24(12-14)29(26,27)20-11-16(6-7-18(20)22)23-21(25)10-15-13-28-19-5-3-2-4-17(15)19/h2-7,11,13-14H,8-10,12H2,1H3,(H,23,25)/t14-/m0/s1

Standard InChI Key:  FIYKACFXLSMUQR-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

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   13.0773   -5.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9760   -7.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1454   -8.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3355   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9841   -8.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6753   -6.5740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5647   -8.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0091   -6.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5635   -7.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2661   -7.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -5.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0982   -8.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2782   -9.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -7.3948    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4216   -7.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5050   -7.3948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8491   -7.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6990   -9.0492    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.1401   -7.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7194   -7.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441   -8.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6410   -8.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5524   -4.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220   -8.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9633   -7.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7033   -6.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9025   -6.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3621   -7.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6249   -7.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19  3  2  0
  2 10  2  0
 19 17  1  0
  5  2  1  0
 17  9  1  0
 10  9  1  0
  1 11  1  0
  8  6  1  0
  9  7  2  0
  5 18  1  0
  6  4  1  0
 15 19  1  0
  7 13  1  0
 12 14  2  0
 14  6  1  0
  2 14  1  0
 14 16  2  0
 13  5  2  0
 11  8  1  0
  4  1  1  0
 15 20  1  0
 20 25  1  0
 24 21  1  0
 21 22  1  0
 22 20  2  0
  1 23  1  6
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525009

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 477.38

Molecular Weight (Monoisotopic): 476.0405

AlogP: 4.41

#Rotatable Bonds: 5

Polar Surface Area: 79.62

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.38

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -1.80

References

1. Lucas SCC, Atkinson SJ, Bamborough P, Barnett H, Chung CW, Gordon L, Mitchell DJ, Phillipou A, Prinjha RK, Sheppard RJ, Tomkinson NCO, Watson RJ, Demont EH..  (2020)  Optimization of Potent ATAD2 and CECR2 Bromodomain Inhibitors with an Atypical Binding Mode.,  63  (10): [PMID:32321240] [10.1021/acs.jmedchem.0c00021]

Source

Source(1):

• Scientific Literature