2-(2-(3,4-dichlorophenyl)acetamido)-N-(5-methylisoxazol-3-yl)thiazole-4-carboxamide

ID: ALA3108834

PubChem CID: 53255422

Max Phase: Preclinical

Molecular Formula: C16H12Cl2N4O3S

Molecular Weight: 411.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NC(=O)c2csc(NC(=O)Cc3ccc(Cl)c(Cl)c3)n2)no1

Standard InChI:  InChI=1S/C16H12Cl2N4O3S/c1-8-4-13(22-25-8)20-15(24)12-7-26-16(19-12)21-14(23)6-9-2-3-10(17)11(18)5-9/h2-5,7H,6H2,1H3,(H,19,21,23)(H,20,22,24)

Standard InChI Key:  UPNLZZGYTQBGLI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   19.4457  -15.8679    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7796  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5960  -15.2037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7667  -16.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0558  -16.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5166  -16.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6024  -17.1570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1807  -15.8581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9177  -17.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1013  -16.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9306  -16.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6415  -15.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2516  -16.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0545  -16.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5483  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1379  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1379  -13.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3692  -14.4070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3170  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9065  -15.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0856  -15.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6752  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0856  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9065  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8543  -15.1179    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6752  -16.5398    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  2  0
  6  8  1  0
  4  6  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
 15 16  1  0
 15 17  2  0
 15 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 22 25  1  0
 21 26  1  0
 16 19  1  0
  2 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108834

   2-[[2-(3,4-dichlorophenyl)acetyl]amino]-N-(5-methyl-1,2-oxazol-3-yl)-1,3-thiazole-4-carboxamide

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: 411.27

Molecular Weight (Monoisotopic): 410.0007

AlogP: 4.18

#Rotatable Bonds: 5

Polar Surface Area: 97.12

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.87

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.11

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -2.69

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