1-Cyclobutyl-N-[6-(2-ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-4-yl]methanesulfonamide

ID: ALA4580425

PubChem CID: 155565806

Max Phase: Preclinical

Molecular Formula: C20H22FN3O3S

Molecular Weight: 403.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(O)c(F)cc1-c1cc(NS(=O)(=O)CC2CCC2)c2cn[nH]c2c1

Standard InChI:  InChI=1S/C20H22FN3O3S/c1-2-13-8-20(25)17(21)9-15(13)14-6-18-16(10-22-23-18)19(7-14)24-28(26,27)11-12-4-3-5-12/h6-10,12,24-25H,2-5,11H2,1H3,(H,22,23)

Standard InChI Key:  VQNDDNOJLMXOHA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   14.6640   -5.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4536   -6.1413    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2451   -5.9274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7475   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4572   -4.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4544   -3.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7457   -3.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1575   -3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8670   -3.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5727   -3.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5701   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8559   -2.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1531   -2.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0395   -4.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0407   -3.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2602   -3.4332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7765   -4.0968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2582   -4.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7473   -5.7354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2757   -2.0429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4547   -6.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8693   -4.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8499   -1.2322    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.5781   -4.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7476   -7.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9632   -7.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7529   -7.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5425   -8.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
 14  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 15  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  8  2  0
  6  8  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  4 19  1  0
 19  2  1  0
 11 20  1  0
  2 21  1  0
  9 22  1  0
 12 23  1  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4580425

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 403.48

Molecular Weight (Monoisotopic): 403.1366

AlogP: 4.18

#Rotatable Bonds: 6

Polar Surface Area: 95.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.69

CX Basic pKa: 2.04

CX LogP: 3.49

CX LogD: 3.32

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -0.95

References

1. Ritzén A, Sørensen MD, Dack KN, Greve DR, Jerre A, Carnerup MA, Rytved KA, Bagger-Bahnsen J..  (2016)  Fragment-Based Discovery of 6-Arylindazole JAK Inhibitors.,  7  (6): [PMID:27326341] [10.1021/acsmedchemlett.6b00087]

Source

Source(1):

• Scientific Literature