3-(5-(2-chlorophenylamino)-1H-indazol-1-yl)-N-(2-hydroxyethyl)benzamide

ID: ALA2376922

PubChem CID: 71602818

Max Phase: Preclinical

Molecular Formula: C22H19ClN4O2

Molecular Weight: 406.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCO)c1cccc(-n2ncc3cc(Nc4ccccc4Cl)ccc32)c1

Standard InChI:  InChI=1S/C22H19ClN4O2/c23-19-6-1-2-7-20(19)26-17-8-9-21-16(12-17)14-25-27(21)18-5-3-4-15(13-18)22(29)24-10-11-28/h1-9,12-14,26,28H,10-11H2,(H,24,29)

Standard InChI Key:  YKQKOWXCFYHZEG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   16.3268   -8.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9650   -9.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8525  -10.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6747   -9.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8324  -11.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0723  -10.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6744   -8.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8329   -9.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8308   -8.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9227   -8.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4561   -8.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5444   -9.6694    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1207   -8.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1261   -9.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4109   -8.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9632   -8.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2514   -8.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2972  -11.6788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3100  -10.2590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2502   -9.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6691  -10.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9379   -8.8507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4315  -10.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5411   -8.0334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9100   -9.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4107   -9.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6540  -11.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4568   -9.5190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8932  -10.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 24  1  0
 14  8  2  0
  1 10  1  0
 21  3  1  0
 11  7  1  0
  9 13  2  0
  2  4  2  0
 15 26  2  0
 25  1  1  0
 16 17  1  0
  7  4  1  0
  8  9  1  0
  5 27  2  0
  7 16  2  0
 29 19  1  0
 17 20  2  0
 20  2  1  0
 28  3  1  0
  8 12  1  0
 27  6  1  0
  6 21  2  0
 13 15  1  0
 29 18  2  0
 24  9  1  0
  4 28  1  0
 22 11  2  0
 26 14  1  0
  6 29  1  0
 23  5  1  0
 28 22  1  0
  3 23  2  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2376922

   3-[5-(2-chloroanilino)indazol-1-yl]-N-(2-hydroxyethyl)benzamide

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: 406.87

Molecular Weight (Monoisotopic): 406.1197

AlogP: 4.14

#Rotatable Bonds: 6

Polar Surface Area: 79.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.12

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.82

References

1. Jiang R, Frackowiak B, Shin Y, Song X, Chen W, Lin L, Cameron MD, Duckett DR, Kamenecka TM..  (2013)  Design and synthesis of 1-aryl-5-anilinoindazoles as c-Jun N-terminal kinase inhibitors.,  23  (9): [PMID:23518277] [10.1016/j.bmcl.2013.02.082]

Source

Source(1):

• Scientific Literature