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

ID: ALA160540

PubChem CID: 44373022

Max Phase: Preclinical

Molecular Formula: C22H18N4O6S2

Molecular Weight: 498.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(/N=C(\S)Nc2cccc(/N=C(/S)Nc3ccc(C(=O)O)c(O)c3)c2)cc1O

Standard InChI:  InChI=1S/C22H18N4O6S2/c27-17-9-13(4-6-15(17)19(29)30)25-21(33)23-11-2-1-3-12(8-11)24-22(34)26-14-5-7-16(20(31)32)18(28)10-14/h1-10,27-28H,(H,29,30)(H,31,32)(H2,23,25,33)(H2,24,26,34)

Standard InChI Key:  TXTOWQIWNZVYJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.9375    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500    0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -1.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -3.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -1.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -2.3792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    0.0958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500    1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -1.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    1.3333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -3.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -2.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667    0.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  2  0
  3 15  1  0
  4 14  1  0
  5  9  2  0
  6  1  2  0
  7  1  1  0
  8  2  1  0
  9 19  1  0
 10  6  1  0
 11 27  1  0
 12  1  1  0
 13  3  2  0
 14 20  1  0
 15 22  1  0
 16  4  2  0
 17  3  1  0
 18  4  1  0
 19 13  1  0
 20 26  1  0
 21 23  2  0
 22 21  1  0
 23 16  1  0
 24  7  2  0
 25  8  2  0
 26 12  2  0
 27 19  2  0
 28  6  1  0
 29  5  1  0
 30  8  1  0
 31  7  1  0
 32 34  2  0
 33 32  1  0
 34 23  1  0
 20 10  2  0
 22 33  2  0
  2  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA160540

   4-[[3-[(4-Carboxy-3-hydroxyphenyl)carbamothioylamino]phenyl]carbamothioylamino]-2-hydroxybenzoic acid

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: 498.54

Molecular Weight (Monoisotopic): 498.0668

AlogP: 4.55

#Rotatable Bonds: 6

Polar Surface Area: 163.84

Molecular Species: ZWITTERION

HBA: 6

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -0.62

CX Basic pKa: 14.72

CX LogP: 5.13

CX LogD: 1.77

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: -0.62

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