4-((3,4-dichlorophenyl)methylsulfonamido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

ID: ALA3108838

PubChem CID: 53255435

Max Phase: Preclinical

Molecular Formula: C17H15Cl2N3O5S2

Molecular Weight: 476.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(NS(=O)(=O)Cc3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C17H15Cl2N3O5S2/c1-11-8-17(20-27-11)22-29(25,26)14-5-3-13(4-6-14)21-28(23,24)10-12-2-7-15(18)16(19)9-12/h2-9,21H,10H2,1H3,(H,20,22)

Standard InChI Key:  UEBJAZZIGBSQMT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.8429   -5.8795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2517   -5.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -5.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328   -6.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -5.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -6.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070   -5.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -5.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -4.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -5.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2942   -4.6445    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -6.2967    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5525   -6.2895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -5.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3889   -4.6497    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7995   -5.3563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2061   -4.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -6.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -5.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -5.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -4.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -5.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3858   -3.8266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0691   -2.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2526   -2.6174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0878   -3.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7972   -3.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4015   -3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2042   -3.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  8 11  1  0
  7 12  1  0
  4  5  1  0
 13  1  1  0
 13 14  1  0
 16 15  2  0
 15 17  2  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 22  2  0
 15 23  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 24 28  1  0
 28 29  1  0
 23 26  1  0
 20 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108838

   4-[(3,4-dichlorophenyl)methylsulfonylamino]-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide

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: 476.36

Molecular Weight (Monoisotopic): 474.9830

AlogP: 4.03

#Rotatable Bonds: 7

Polar Surface Area: 118.37

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.02

CX Basic pKa: 0.38

CX LogP: 3.08

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -2.21

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]

Source

Source(1):

• Scientific Literature