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

ID: ALA4228519

PubChem CID: 145967960

Max Phase: Preclinical

Molecular Formula: C21H18Cl2N4O3S2

Molecular Weight: 509.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oncc1-c1nc(-n2nc(C(=O)O)c(-c3cc(Cl)cc(Cl)c3)c2C)sc1SC(C)C

Standard InChI:  InChI=1S/C21H18Cl2N4O3S2/c1-9(2)31-20-17(15-8-24-30-11(15)4)25-21(32-20)27-10(3)16(18(26-27)19(28)29)12-5-13(22)7-14(23)6-12/h5-9H,1-4H3,(H,28,29)

Standard InChI Key:  IGLHDTMKAYYXMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   25.5558  -11.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3730  -11.9071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6273  -11.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9644  -10.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3056  -11.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4045  -10.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0649  -11.3605    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.7267  -10.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4753  -10.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6581  -10.1025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5305  -10.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3613  -10.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5849   -9.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9769  -10.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1506  -11.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9268  -11.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9631   -9.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5036  -11.1347    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.6724  -11.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4492  -12.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0643  -12.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0746  -12.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2620  -12.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4060  -13.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5455  -11.7273    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.4150   -9.0286    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.9521   -9.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7693   -9.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0228   -8.6628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3623   -8.1815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7006   -8.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2487  -10.1014    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  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 27  1  0
  9 27  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228519

   ---

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: 509.44

Molecular Weight (Monoisotopic): 508.0197

AlogP: 6.77

#Rotatable Bonds: 6

Polar Surface Area: 94.04

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.11

CX Basic pKa: 0.15

CX LogP: 6.46

CX LogD: 3.00

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -1.39

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