N-[4-(4-Hydroxy-3-methyl-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

ID: ALA138010

PubChem CID: 10522547

Max Phase: Preclinical

Molecular Formula: C17H16N2O3S2

Molecular Weight: 360.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)Nc2nc(-c3ccc(O)c(C)c3)cs2)cc1

Standard InChI:  InChI=1S/C17H16N2O3S2/c1-11-3-6-14(7-4-11)24(21,22)19-17-18-15(10-23-17)13-5-8-16(20)12(2)9-13/h3-10,20H,1-2H3,(H,18,19)

Standard InChI Key:  JNLUXBUTTJOENI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.4792   -2.5167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -1.9167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -3.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  3  1  0
  7  6  1  0
  8  1  1  0
  9  5  1  0
 10  1  2  0
 11  1  2  0
 12  9  1  0
 13 12  2  0
 14 16  2  0
 15  9  2  0
 16 15  1  0
 17  8  2  0
 18  8  1  0
 19 18  2  0
 20 17  1  0
 21 19  1  0
 22 14  1  0
 23 13  1  0
 24 21  1  0
 21 20  2  0
  7  5  2  0
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA138010

   N-[4-(4-Hydroxy-3-methyl-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

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: 360.46

Molecular Weight (Monoisotopic): 360.0602

AlogP: 3.93

#Rotatable Bonds: 4

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.78

CX Basic pKa: ┄

CX LogP: 4.56

CX LogD: 4.02

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -1.57

References

1. Röver S, Cesura AM, Huguenin P, Kettler R, Szente A..  (1997)  Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high-affinity inhibitors of kynurenine 3-hydroxylase.,  40  (26): [PMID:9435907] [10.1021/jm970467t]

Source

Source(1):

• Scientific Literature