4-({5-[3-(2-chloro-4-methylphenyl)pyridin-4-yl]-1,3-thiazol-2-yl}amino)phenol

ID: ALA5278261

Max Phase: Preclinical

Molecular Formula: C21H16ClN3OS

Molecular Weight: 393.90

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2cnccc2-c2cnc(Nc3ccc(O)cc3)s2)c(Cl)c1

Standard InChI:  InChI=1S/C21H16ClN3OS/c1-13-2-7-16(19(22)10-13)18-11-23-9-8-17(18)20-12-24-21(27-20)25-14-3-5-15(26)6-4-14/h2-12,26H,1H3,(H,24,25)

Standard InChI Key:  QYDBOFPHPMYWDO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    2.6013    0.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3471    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4137   -0.6186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7354   -1.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9926   -0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    0.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958   -0.0349    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    0.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016    1.2428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306    1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445    0.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    0.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780   -1.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777   -1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5649   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1499   -1.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1514   -1.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -2.3894    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508    0.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9778    0.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    2.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257    1.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137    2.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645   -2.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  6  7  1  0
  8  7  1  0
  8  9  1  0
  9 10  2  0
 11 10  1  0
  7 11  2  0
  9 12  1  0
 12 13  1  0
 14  5  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 14 19  1  0
 19 18  2  0
 15 20  1  0
 21 13  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 13 25  1  0
 23 26  1  0
 17 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278261

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 393.90

Molecular Weight (Monoisotopic): 393.0703

AlogP: 6.28

#Rotatable Bonds: 4

Polar Surface Area: 58.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.28

CX Basic pKa: 3.91

CX LogP: 5.64

CX LogD: 5.64

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -1.10

References

1. Manetti F..  (2018)  Recent advances in the rational design and development of LIM kinase inhibitors are not enough to enter clinical trials.,  155  [PMID:29908439] [10.1016/j.ejmech.2018.06.016]

Source

Source(1):

• Scientific Literature