4-[3-(2,2,4,4,7-Pentamethyl-thiochroman-6-yl)-thioureido]-benzenesulfonamide

ID: ALA6499

PubChem CID: 10366476

Max Phase: Preclinical

Molecular Formula: C21H27N3O2S3

Molecular Weight: 449.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1/N=C(\S)Nc1ccc(S(N)(=O)=O)cc1)C(C)(C)CC(C)(C)S2

Standard InChI:  InChI=1S/C21H27N3O2S3/c1-13-10-18-16(20(2,3)12-21(4,5)28-18)11-17(13)24-19(27)23-14-6-8-15(9-7-14)29(22,25)26/h6-11H,12H2,1-5H3,(H2,22,25,26)(H2,23,24,27)

Standard InChI Key:  JXHVRXRRSSBGPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.0333   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7458   -2.1667    0.0000 S   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
    0.3917   -0.9167    0.0000 C   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
    1.1042   -0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4000   -1.7417    0.0000 C   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
    5.1875   -1.3250    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
    5.6167   -2.9167    0.0000 N   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
    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
    1.1167   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  2  0
  3  8  2  0
  4  2  1  0
  5 17  1  0
  6  3  1  0
  7  9  1  0
  8  7  1  0
  9  5  2  0
 10  4  1  0
 11  1  1  0
 12 13  1  0
 13  7  2  0
 14  6  1  0
 15  1  2  0
 16  1  2  0
 17 22  1  0
 18  5  1  0
 19  1  1  0
 20 11  2  0
 21 11  1  0
 22 24  1  0
 23 20  1  0
 24 21  2  0
 25  6  1  0
 26  6  1  0
 27 10  1  0
 28 10  1  0
 29 13  1  0
 22 23  2  0
  3  2  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA6499

   1-(2,2,4,4,7-pentamethyl-3H-thiochromen-6-yl)-3-(4-sulfamoylphenyl)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: 449.67

Molecular Weight (Monoisotopic): 449.1265

AlogP: 5.22

#Rotatable Bonds: 3

Polar Surface Area: 84.55

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.19

CX Basic pKa: 7.06

CX LogP: 6.21

CX LogD: 6.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.00

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