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

ID: ALA4228847

PubChem CID: 124119768

Max Phase: Preclinical

Molecular Formula: C24H21Cl2N3O3S2

Molecular Weight: 534.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c(C)nn(-c3nc(-c4ccc(Cl)c(Cl)c4)c(SC(C)C)s3)c2C(=O)O)cc1

Standard InChI:  InChI=1S/C24H21Cl2N3O3S2/c1-12(2)33-23-20(15-7-10-17(25)18(26)11-15)27-24(34-23)29-21(22(30)31)19(13(3)28-29)14-5-8-16(32-4)9-6-14/h5-12H,1-4H3,(H,30,31)

Standard InChI Key:  UZRUYXNBGCPHKM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   27.0044   -4.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8216   -4.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0760   -3.6642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4130   -3.1821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7543   -3.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8558   -3.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.9266   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1094   -2.6326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4070   -1.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2205   -2.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7016   -1.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.1140   -5.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5141   -1.4921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.8505    0.0044    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.9549   -3.6649    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.1237   -4.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9005   -4.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5156   -5.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7102   -5.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2292   -5.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5605   -6.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3776   -6.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8550   -5.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0802   -7.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2675   -6.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  1  1  0
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  9 10  1  0
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  3  6  1  0
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  9 11  1  0
  5 17  1  0
  1 18  1  0
  2 19  1  0
 19 20  1  0
 19 21  2  0
 13 22  1  0
 14 23  1  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 18 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 18  1  0
 30 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228847

   ---

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: 534.49

Molecular Weight (Monoisotopic): 533.0401

AlogP: 7.49

#Rotatable Bonds: 7

Polar Surface Area: 77.24

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.38

CX Basic pKa: 0.45

CX LogP: 7.20

CX LogD: 3.79

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.25

Np Likeness Score: -1.32

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