4-[3-(2,2,4,4,7-Pentamethyl-thiochroman-6-yl)-thioureido]-benzoic acid ethyl ester

ID: ALA6825

PubChem CID: 11293676

Max Phase: Preclinical

Molecular Formula: C24H30N2O2S2

Molecular Weight: 442.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(N/C(S)=N/c2cc3c(cc2C)SC(C)(C)CC3(C)C)cc1

Standard InChI:  InChI=1S/C24H30N2O2S2/c1-7-28-21(27)16-8-10-17(11-9-16)25-22(29)26-19-13-18-20(12-15(19)2)30-24(5,6)14-23(18,3)4/h8-13H,7,14H2,1-6H3,(H2,25,26,29)

Standard InChI Key:  PEDXWASSKCBZSV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.0333   -0.9250    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
    1.8250   -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
   -2.4583   -1.7542    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
    5.4042   -2.1250    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
   -2.4583   -0.9250    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
    1.8292   -1.7292    0.0000 S   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
    6.1167   -1.7042    0.0000 O   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
    5.4042   -2.9500    0.0000 O   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
    3.2542   -1.7250    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
    1.1167   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  8  2  0
  5  2  1  0
  6 12  1  0
  7  2  1  0
  8  6  1  0
  9  3  1  0
 10  1  1  0
 11 16  1  0
 12 10  2  0
 13  9  1  0
 14  4  1  0
 15  4  1  0
 16 18  2  0
 17 11  2  0
 18 23  1  0
 19 22  2  0
 20 14  1  0
 21 11  1  0
 22 20  1  0
 23 20  2  0
 24  5  1  0
 25  5  1  0
 26  9  1  0
 27  9  1  0
 28 12  1  0
 29 21  1  0
 30 29  1  0
  6  7  2  0
  5 13  1  0
 19 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA6825

   ethyl 4-[(2,2,4,4,7-pentamethyl-3H-thiochromen-6-yl)carbamothioylamino]benzoate

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: 442.65

Molecular Weight (Monoisotopic): 442.1749

AlogP: 6.75

#Rotatable Bonds: 4

Polar Surface Area: 50.69

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.27

CX Basic pKa: 7.13

CX LogP: 7.98

CX LogD: 7.80

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.24

Np Likeness Score: -0.66

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