rac-2-(4-(4-chloro-3-fluorophenyl)-5-cyano-6-oxo-1,6-dihydropyrimidin-2-ylthio)-N-(4-sulfamoylphenyl)propanamide

ID: ALA2382403

PubChem CID: 136242878

Max Phase: Preclinical

Molecular Formula: C20H15ClFN5O4S2

Molecular Weight: 507.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Sc1nc(-c2ccc(Cl)c(F)c2)c(C#N)c(=O)[nH]1)C(=O)Nc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C20H15ClFN5O4S2/c1-10(18(28)25-12-3-5-13(6-4-12)33(24,30)31)32-20-26-17(14(9-23)19(29)27-20)11-2-7-15(21)16(22)8-11/h2-8,10H,1H3,(H,25,28)(H2,24,30,31)(H,26,27,29)

Standard InChI Key:  DGPLKIFFYFAJEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    2.3320  -13.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237  -13.0938    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108  -13.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431  -11.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6420  -12.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568  -13.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732  -12.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704  -11.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3550  -11.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130  -12.6825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833  -11.4374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993  -11.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2122  -11.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024  -12.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9282  -11.8418    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6411  -11.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3570  -11.8396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0678  -11.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0690  -10.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3531  -10.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6361  -10.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3528   -9.3656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7841  -10.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4986   -9.7819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7806  -11.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7793  -12.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4929  -13.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2083  -12.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2057  -11.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4915  -11.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2091  -10.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9234  -13.0771    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.9187  -11.4213    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5  2  1  0
  2 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 23 24  3  0
 19 23  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 18 25  1  0
 13 31  1  0
 28 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2382403

   ---

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: 507.96

Molecular Weight (Monoisotopic): 507.0238

AlogP: 2.87

#Rotatable Bonds: 6

Polar Surface Area: 158.80

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.98

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 2.05

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -2.46

References

1. Dragovich PS, Fauber BP, Corson LB, Ding CZ, Eigenbrot C, Ge H, Giannetti AM, Hunsaker T, Labadie S, Liu Y, Malek S, Pan B, Peterson D, Pitts K, Purkey HE, Sideris S, Ultsch M, VanderPorten E, Wei B, Xu Q, Yen I, Yue Q, Zhang H, Zhang X..  (2013)  Identification of substituted 2-thio-6-oxo-1,6-dihydropyrimidines as inhibitors of human lactate dehydrogenase.,  23  (11): [PMID:23628333] [10.1016/j.bmcl.2013.04.001]

2. Vullo D, Supuran CT, Scozzafava A, De Simone G, Monti SM, Alterio V, Carta F..  (2016)  Kinetic and X-ray crystallographic investigations of substituted 2-thio-6-oxo-1,6-dihydropyrimidine-benzenesulfonamides acting as carbonic anhydrase inhibitors.,  24  (16): [PMID:27316543] [10.1016/j.bmc.2016.06.005]

Source

Source(1):

• Scientific Literature