2-(3,4-dichlorophenyl)-N-(2-(N-(5-methylisoxazol-3-yl)sulfamoyl)ethyl)acetamide

ID: ALA3108833

PubChem CID: 53255442

Max Phase: Preclinical

Molecular Formula: C14H15Cl2N3O4S

Molecular Weight: 392.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)CCNC(=O)Cc2ccc(Cl)c(Cl)c2)no1

Standard InChI:  InChI=1S/C14H15Cl2N3O4S/c1-9-6-13(18-23-9)19-24(21,22)5-4-17-14(20)8-10-2-3-11(15)12(16)7-10/h2-3,6-7H,4-5,8H2,1H3,(H,17,20)(H,18,19)

Standard InChI Key:  TZSMCCAKJZATDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   20.0992   -6.4948    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5116   -5.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6870   -5.7805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2325   -6.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9479   -6.9076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6642   -6.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3838   -6.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8146   -6.9094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7991   -6.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3137   -6.7479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5309   -6.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5313   -5.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3163   -5.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5708   -4.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2299   -5.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5196   -6.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8041   -6.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8057   -5.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0910   -5.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3771   -5.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3823   -6.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0975   -6.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6701   -6.9267    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.6617   -5.2674    0.0000 Cl  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
  1  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  9 13  1  0
 13 14  1  0
  8 11  1  0
  7  1  1  0
  5  6  1  0
  4 15  2  0
  4 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 21 23  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108833

   2-(3,4-dichlorophenyl)-N-[2-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]ethyl]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: 392.26

Molecular Weight (Monoisotopic): 391.0160

AlogP: 2.39

#Rotatable Bonds: 7

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: 6.27

CX Basic pKa: 0.42

CX LogP: 1.72

CX LogD: 0.96

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.75

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