2-(4-methoxy-3-methylphenyl)-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide

ID: ALA3108851

PubChem CID: 53255406

Max Phase: Preclinical

Molecular Formula: C20H21N3O5S

Molecular Weight: 415.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC(=O)Nc2ccc(S(=O)(=O)Nc3cc(C)on3)cc2)cc1C

Standard InChI:  InChI=1S/C20H21N3O5S/c1-13-10-15(4-9-18(13)27-3)12-20(24)21-16-5-7-17(8-6-16)29(25,26)23-19-11-14(2)28-22-19/h4-11H,12H2,1-3H3,(H,21,24)(H,22,23)

Standard InChI Key:  XBKZJHIKQFSOMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.2185   -5.0253    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6291   -5.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0357   -5.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6725   -6.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9623   -6.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2535   -6.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5480   -6.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -6.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373   -5.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5469   -5.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2517   -5.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -6.6650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0899   -6.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7925   -6.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5035   -6.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5035   -5.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7925   -5.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0899   -5.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2154   -4.2021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8987   -2.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0822   -2.9930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9174   -3.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6268   -4.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2311   -3.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0338   -3.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6717   -5.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -6.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -5.0284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299   -4.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  5  6  1  0
 12  4  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
  1 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 20 24  1  0
 24 25  1  0
 19 22  1  0
 16  1  1  0
  4 26  2  0
  8 27  1  0
  9 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108851

   2-(4-methoxy-3-methylphenyl)-N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide

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: 415.47

Molecular Weight (Monoisotopic): 415.1202

AlogP: 3.28

#Rotatable Bonds: 7

Polar Surface Area: 110.53

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.38

CX LogP: 3.05

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -1.99

References

1. Brimacombe KR, Walsh MJ, Liu L, Vásquez-Valdivieso MG, Morgan HP, McNae I, Fothergill-Gilmore LA, Michels PA, Auld DS, Simeonov A, Walkinshaw MD, Shen M, Boxer MB..  (2014)  Identification of ML251, a Potent Inhibitor of T. brucei and T. cruzi Phosphofructokinase.,  5  (1): [PMID:24900769] [10.1021/ml400259d]

2. Miana GE, Ribone SR, Vera DMA, Sánchez-Moreno M, Mazzieri MR, Quevedo MA..  (2019)  Design, synthesis and molecular docking studies of novel N-arylsulfonyl-benzimidazoles with anti Trypanosoma cruzi activity.,  165  [PMID:30641409] [10.1016/j.ejmech.2019.01.013]

Source

Source(1):

• Scientific Literature