ethyl 4-[4-[4-carboxy-3-hydroxyanilino(thioxo)methylamino]anilino(thioxo)methylamino]-2-hydroxybenzoic acid

ID: ALA160315

PubChem CID: 44373186

Max Phase: Preclinical

Molecular Formula: C26H26N4O6S2

Molecular Weight: 554.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(/N=C(\S)Nc2ccc(/N=C(/S)Nc3ccc(C(=O)OCC)c(O)c3)cc2)cc1O

Standard InChI:  InChI=1S/C26H26N4O6S2/c1-3-35-23(33)19-11-9-17(13-21(19)31)29-25(37)27-15-5-7-16(8-6-15)28-26(38)30-18-10-12-20(22(32)14-18)24(34)36-4-2/h5-14,31-32H,3-4H2,1-2H3,(H2,27,29,37)(H2,28,30,38)

Standard InChI Key:  BBDTZWJCLCJOJN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
    4.7500   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -5.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -4.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    0.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667    0.1083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -2.9250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    1.3458    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417    2.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -6.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    0.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -3.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625    1.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -4.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750    1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917    1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  2  0
  3 16  2  0
  4 13  2  0
  5 10  2  0
  6  1  2  0
  7  2  1  0
  8  1  1  0
  9  6  1  0
 10 20  1  0
 11  1  1  0
 12 26  1  0
 13 19  1  0
 14  3  1  0
 15  4  1  0
 16 23  1  0
 17  4  1  0
 18  3  1  0
 19 25  1  0
 20 14  1  0
 21  7  2  0
 22  8  2  0
 23 31  2  0
 24 15  1  0
 25 11  2  0
 26 20  2  0
 27  5  1  0
 28  6  1  0
 29  7  1  0
 30  8  1  0
 31 34  1  0
 32 24  1  0
 33 32  2  0
 34 24  2  0
 35 29  1  0
 36 30  1  0
 37 35  1  0
 38 36  1  0
 19  9  2  0
 33 23  1  0
  2  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA160315

   Ethyl 4-[[4-[(4-ethoxycarbonyl-3-hydroxyphenyl)carbamothioylamino]phenyl]carbamothioylamino]-2-hydroxybenzoate

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: 554.65

Molecular Weight (Monoisotopic): 554.1294

AlogP: 5.51

#Rotatable Bonds: 8

Polar Surface Area: 141.84

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.54

CX Basic pKa: 14.90

CX LogP: 9.27

CX LogD: 8.55

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.09

Np Likeness Score: -0.64

References

1. Phuong T, Khac-Minh T, Van Ha NT, Ngoc Phuong HT..  (2004)  Synthesis and antifungal activities of phenylenedithioureas.,  14  (3): [PMID:14741262] [10.1016/j.bmcl.2003.11.044]

Source

Source(1):

• Scientific Literature