4-[3-(2,2,4,4-Tetramethyl-thiochroman-6-yl)-thioureido]-benzenesulfonamide

ID: ALA6524

PubChem CID: 10478135

Max Phase: Preclinical

Molecular Formula: C20H25N3O2S3

Molecular Weight: 435.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC(C)(C)c2cc(N/C(S)=N/c3ccc(S(N)(=O)=O)cc3)ccc2S1

Standard InChI:  InChI=1S/C20H25N3O2S3/c1-19(2)12-20(3,4)27-17-10-7-14(11-16(17)19)23-18(26)22-13-5-8-15(9-6-13)28(21,24)25/h5-11H,12H2,1-4H3,(H2,21,24,25)(H2,22,23,26)

Standard InChI Key:  HNXZQKZCCDWHKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.4042   -2.1250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -2.1667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -1.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -1.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -2.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3 15  2  0
  4 13  2  0
  5  3  1  0
  6 18  2  0
  7  2  1  0
  8  1  1  0
  9  4  1  0
 10  5  1  0
 11  1  2  0
 12  1  2  0
 13 21  1  0
 14  4  1  0
 15 17  1  0
 16  1  1  0
 17  9  1  0
 18 22  1  0
 19  8  2  0
 20  8  1  0
 21 24  1  0
 22 17  2  0
 23 19  1  0
 24 20  2  0
 25  5  1  0
 26  5  1  0
 27  7  1  0
 28  7  1  0
 21 23  2  0
  3  6  1  0
 10  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA6524

   1-(4-sulfamoylphenyl)-3-(2,2,4,4-tetramethyl-3H-thiochromen-6-yl)thiourea

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: 435.64

Molecular Weight (Monoisotopic): 435.1109

AlogP: 4.92

#Rotatable Bonds: 3

Polar Surface Area: 84.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.68

CX Basic pKa: 5.07

CX LogP: 5.10

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -1.15

References

1. Liu S, Brown CW, Berlin KD, Dhar A, Guruswamy S, Brown D, Gardner GJ, Birrer MJ, Benbrook DM..  (2004)  Synthesis of flexible sulfur-containing heteroarotinoids that induce apoptosis and reactive oxygen species with discrimination between malignant and benign cells.,  47  (4): [PMID:14761202] [10.1021/jm030346v]

Source

Source(1):

• Scientific Literature