4-(4-(2-(3,4-dichlorophenyl)acetamido)phenylsulfonamido)benzoic acid

ID: ALA3108863

PubChem CID: 53255425

Max Phase: Preclinical

Molecular Formula: C21H16Cl2N2O5S

Molecular Weight: 479.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Cl)c(Cl)c1)Nc1ccc(S(=O)(=O)Nc2ccc(C(=O)O)cc2)cc1

Standard InChI:  InChI=1S/C21H16Cl2N2O5S/c22-18-10-1-13(11-19(18)23)12-20(26)24-15-6-8-17(9-7-15)31(29,30)25-16-4-2-14(3-5-16)21(27)28/h1-11,25H,12H2,(H,24,26)(H,27,28)

Standard InChI Key:  WDKMQRBCNNTVHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  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
   12.9635   -2.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6734   -3.2717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9591   -2.0498    0.0000 O   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
 26 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108863

   4-[[4-[[2-(3,4-Dichlorophenyl)acetyl]amino]phenyl]sulfonylamino]benzoic acid

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: 479.34

Molecular Weight (Monoisotopic): 478.0157

AlogP: 4.67

#Rotatable Bonds: 7

Polar Surface Area: 112.57

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.49

CX Basic pKa: ┄

CX LogP: 4.40

CX LogD: 1.52

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -1.53

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