4-[({[4-({[(4-carboxyphenyl)amino]carbonothioyl}amino)phenyl]amino}carbonothioyl)amino]benzoic acid

ID: ALA345363

Cas Number: 442847-55-4

PubChem CID: 44373284

Max Phase: Preclinical

Molecular Formula: C22H18N4O4S2

Molecular Weight: 466.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(/N=C(\S)Nc2ccc(/N=C(\S)Nc3ccc(C(=O)O)cc3)cc2)cc1

Standard InChI:  InChI=1S/C22H18N4O4S2/c27-19(28)13-1-5-15(6-2-13)23-21(31)25-17-9-11-18(12-10-17)26-22(32)24-16-7-3-14(4-8-16)20(29)30/h1-12H,(H,27,28)(H,29,30)(H2,23,25,31)(H2,24,26,32)

Standard InChI Key:  WOWXXENYGIWZDW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    2.2792   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -4.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -1.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -5.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -1.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -4.1542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    0.1208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667    1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125   -7.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -6.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -5.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -3.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875    0.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -6.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3 12  1  0
  4 11  1  0
  5  1  2  0
  6  2  2  0
  7  1  1  0
  8 22  1  0
  9  1  1  0
 10  2  1  0
 11 17  2  0
 12 18  2  0
 13  3  2  0
 14  4  2  0
 15 27  2  0
 16 25  2  0
 17 28  1  0
 18 26  1  0
 19  6  1  0
 20  7  1  0
 21  5  1  0
 22 29  1  0
 23  3  1  0
 24  4  1  0
 25 19  1  0
 26 19  2  0
 27 20  1  0
 28 20  2  0
 29 32  2  0
 30 21  2  0
 31 30  1  0
 32 21  1  0
 15 11  1  0
 22 31  2  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA345363

   Benzoic acid, 4,4'-[1,4-phenylenebis(iminocarbonothioylimino)]bis-

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: 466.54

Molecular Weight (Monoisotopic): 466.0769

AlogP: 5.14

#Rotatable Bonds: 6

Polar Surface Area: 123.38

Molecular Species: ZWITTERION

HBA: 4

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -0.49

CX Basic pKa: 15.00

CX LogP: 4.97

CX LogD: 1.51

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.17

Np Likeness Score: -0.61

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