1-(2-Methyl-4-nitro-phenyl)-3-(2,2,4,4-tetramethyl-thiochroman-6-yl)-thiourea

ID: ALA7074

PubChem CID: 10216399

Max Phase: Preclinical

Molecular Formula: C21H25N3O2S2

Molecular Weight: 415.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc([N+](=O)[O-])ccc1/N=C(\S)Nc1ccc2c(c1)C(C)(C)CC(C)(C)S2

Standard InChI:  InChI=1S/C21H25N3O2S2/c1-13-10-15(24(25)26)7-8-17(13)23-19(27)22-14-6-9-18-16(11-14)20(2,3)12-21(4,5)28-18/h6-11H,12H2,1-5H3,(H2,22,23,27)

Standard InChI Key:  CMVYAMQKLILTCP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.4042   -2.1250    0.0000 N   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   -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
   -1.7458   -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
    4.6792   -1.7167    0.0000 C   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
   -2.4583   -1.7542    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
    1.1042   -0.5000    0.0000 N   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
    3.9542   -0.4792    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
    5.4125   -2.9500    0.0000 O   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
    6.1167   -1.7042    0.0000 O   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
    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
    3.2542   -1.7250    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
   -1.1625    0.0750    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
   -3.1750   -1.3417    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
    3.9500    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  2  0
  3  6  1  0
  4 18  2  0
  5  4  1  0
  6 20  2  0
  7  1  1  0
  8 10  1  0
  9  3  1  0
 10 22  1  0
 11  2  1  0
 12  7  2  0
 13 12  1  0
 14  5  1  0
 15  1  1  0
 16  2  1  0
 17  1  2  0
 18 19  1  0
 19 11  1  0
 20 23  1  0
 21  7  1  0
 22 21  2  0
 23 19  2  0
 24  5  1  0
 25  5  1  0
 26  9  1  0
 27  9  1  0
 28 13  1  0
 13 10  2  0
  4  6  1  0
 14  9  1  0
M  CHG  2   1   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA7074

   1-(2-methyl-4-nitrophenyl)-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: 415.58

Molecular Weight (Monoisotopic): 415.1388

AlogP: 6.48

#Rotatable Bonds: 3

Polar Surface Area: 67.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.72

CX Basic pKa: 4.76

CX LogP: 6.84

CX LogD: 6.27

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.20

Np Likeness Score: -1.20

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