(+/-)-2-Methoxy-2-phenyl-N-(3-(3-sulfamoylphenyl)-1Hindazol-5-yl)acetamide

ID: ALA3330401

Max Phase: Preclinical

Molecular Formula: C22H20N4O4S

Molecular Weight: 436.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(C(=O)Nc1ccc2[nH]nc(-c3cccc(S(N)(=O)=O)c3)c2c1)c1ccccc1

Standard InChI:  InChI=1S/C22H20N4O4S/c1-30-21(14-6-3-2-4-7-14)22(27)24-16-10-11-19-18(13-16)20(26-25-19)15-8-5-9-17(12-15)31(23,28)29/h2-13,21H,1H3,(H,24,27)(H,25,26)(H2,23,28,29)

Standard InChI Key:  WBKWIGZIJLEGEF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    5.1638   -6.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2696   -4.4759    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9790   -4.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2596   -3.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948   -6.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5936   -7.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3085   -7.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3067   -5.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0221   -6.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0224   -7.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8129   -7.2761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013   -6.6035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8125   -5.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2156   -5.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0412   -5.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446   -4.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0231   -3.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1938   -3.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7942   -4.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6908   -5.1854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8802   -5.7797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4512   -5.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357   -6.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262   -5.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -6.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089   -7.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0274   -7.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -7.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1587   -7.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -4.9549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1685   -4.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  2  4  2  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16  2  1  0
  2 20  1  0
  5 21  1  0
 21  1  1  0
  1 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  1 29  2  0
 22 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3330401

   ---

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: 436.49

Molecular Weight (Monoisotopic): 436.1205

AlogP: 3.20

#Rotatable Bonds: 6

Polar Surface Area: 127.17

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.04

CX Basic pKa: 1.68

CX LogP: 2.94

CX LogD: 2.93

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.70

References

1. Laufer R, Ng G, Liu Y, Patel NK, Edwards LG, Lang Y, Li SW, Feher M, Awrey DE, Leung G, Beletskaya I, Plotnikova O, Mason JM, Hodgson R, Wei X, Mao G, Luo X, Huang P, Green E, Kiarash R, Lin DC, Harris-Brandts M, Ban F, Nadeem V, Mak TW, Pan GJ, Qiu W, Chirgadze NY, Pauls HW..  (2014)  Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides.,  22  (17): [PMID:25043312] [10.1016/j.bmc.2014.06.027]

Source

Source(1):

• Scientific Literature