N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)-2-phenylacetamide

ID: ALA3108842

PubChem CID: 5220784

Max Phase: Preclinical

Molecular Formula: C18H17N3O4S

Molecular Weight: 371.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(NC(=O)Cc3ccccc3)cc2)no1

Standard InChI:  InChI=1S/C18H17N3O4S/c1-13-11-17(20-25-13)21-26(23,24)16-9-7-15(8-10-16)19-18(22)12-14-5-3-2-4-6-14/h2-11H,12H2,1H3,(H,19,22)(H,20,21)

Standard InChI Key:  SAKCVBSZNULADI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.4178   -4.6910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8284   -5.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2350   -4.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -5.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1616   -6.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528   -5.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -6.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358   -5.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366   -5.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7462   -4.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4510   -5.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5814   -6.3307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892   -5.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9919   -6.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7028   -5.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7028   -5.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9919   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892   -5.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4147   -3.8678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0980   -2.5729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2815   -2.6587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167   -3.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8261   -3.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4304   -3.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2331   -3.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8711   -5.1036    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA3108842

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

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: 371.42

Molecular Weight (Monoisotopic): 371.0940

AlogP: 2.97

#Rotatable Bonds: 6

Polar Surface Area: 101.30

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.38

CX LogP: 2.69

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -2.16

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