Ethyl 3-(4-(2-(3,4-dichlorophenyl)acetamido)phenylsulfonamido)benzoate

ID: ALA3108862

PubChem CID: 53255416

Max Phase: Preclinical

Molecular Formula: C23H20Cl2N2O5S

Molecular Weight: 507.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cccc(NS(=O)(=O)c2ccc(NC(=O)Cc3ccc(Cl)c(Cl)c3)cc2)c1

Standard InChI:  InChI=1S/C23H20Cl2N2O5S/c1-2-32-23(29)16-4-3-5-18(14-16)27-33(30,31)19-9-7-17(8-10-19)26-22(28)13-15-6-11-20(24)21(25)12-15/h3-12,14,27H,2,13H2,1H3,(H,26,28)

Standard InChI Key:  TYULLOFEMGFUPS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   10.8419   -4.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4248   -4.1091    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8321   -3.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0150   -3.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -5.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8789   -5.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5884   -5.7488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2963   -5.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9989   -5.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7098   -5.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7098   -4.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9989   -4.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2962   -4.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -4.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4601   -5.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4637   -4.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559   -4.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0481   -4.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526   -5.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609   -5.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484   -5.7657    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3421   -4.1256    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.1333   -4.5164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5528   -4.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2610   -4.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2580   -3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5411   -2.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8359   -3.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9701   -4.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9731   -5.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6764   -4.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3855   -4.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0918   -4.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  2  4  2  0
  6  5  1  0
  7  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 11  2  1  0
  6 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 18 22  1  0
  2 23  1  0
 23  1  1  0
  1 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28  1  1  0
 25 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108862

   Ethyl 3-[[4-[[2-(3,4-dichlorophenyl)acetyl]amino]phenyl]sulfonylamino]benzoate

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: 507.40

Molecular Weight (Monoisotopic): 506.0470

AlogP: 5.15

#Rotatable Bonds: 8

Polar Surface Area: 101.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.80

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 4.97

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -1.72

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