4-(3,5-dichlorophenyl)-1-(5-(isopropylthio)-4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)-5-methyl-1H-pyrazole-3-carboxylic acid

ID: ALA4228776

PubChem CID: 145986569

Max Phase: Preclinical

Molecular Formula: C21H19Cl2N5O2S2

Molecular Weight: 508.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(-c2cc(Cl)cc(Cl)c2)c(C(=O)O)nn1-c1nc(-c2cnn(C)c2)c(SC(C)C)s1

Standard InChI:  InChI=1S/C21H19Cl2N5O2S2/c1-10(2)31-20-17(13-8-24-27(4)9-13)25-21(32-20)28-11(3)16(18(26-28)19(29)30)12-5-14(22)7-15(23)6-12/h5-10H,1-4H3,(H,29,30)

Standard InChI Key:  YOHBTIMPXPGOGI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   35.9110   -4.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7282   -4.9816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9825   -4.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3196   -3.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6608   -4.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7597   -3.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4201   -4.4350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.0819   -3.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8305   -3.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0133   -3.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8857   -3.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7165   -3.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9401   -2.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3321   -3.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5058   -4.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2821   -4.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3183   -2.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8588   -4.2092    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.0276   -5.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8044   -5.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4195   -5.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4298   -5.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6172   -5.5556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7612   -6.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9007   -4.8018    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.7702   -2.1031    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.3073   -2.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1245   -2.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3780   -1.7418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7175   -1.2606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0558   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7185   -0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  2  0
  3  6  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  5 11  1  0
  4 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  1 22  1  0
 22 23  2  0
 22 24  1  0
 15 25  1  0
 13 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 27  2  0
  9 27  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228776

   ---

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: 508.46

Molecular Weight (Monoisotopic): 507.0357

AlogP: 6.21

#Rotatable Bonds: 6

Polar Surface Area: 85.83

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.12

CX Basic pKa: 1.55

CX LogP: 6.15

CX LogD: 2.86

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.70

References

1. Cooper AB, Ciblat S, Shipps G, Levine J, Kostura M, Oza V, Constantineau-Forget L, Dery M, Grand-Maitre C, Bruneau-Latour N, Bellavance E, Patane M, Siddiqui A, Luther M..  (2017)  1-Thiazol-2-yl-N-3-methyl-1H-pyrozole-5-carboxylic acid derivatives as antitumor agents.,  27  (18): [PMID:28844391] [10.1016/j.bmcl.2017.08.003]

Source

Source(1):

• Scientific Literature