methyl 4-[4-[4-methyloxycarbonylanilino(thioxo)methylamino]anilino(thioxo)methylamino]benzoate

ID: ALA159057

PubChem CID: 44372957

Max Phase: Preclinical

Molecular Formula: C24H22N4O4S2

Molecular Weight: 494.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H22N4O4S2/c1-31-21(29)15-3-7-17(8-4-15)25-23(33)27-19-11-13-20(14-12-19)28-24(34)26-18-9-5-16(6-10-18)22(30)32-2/h3-14H,1-2H3,(H2,25,27,33)(H2,26,28,34)

Standard InChI Key:  PBDOSLCTGMCIND-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.3667   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8625    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -4.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -1.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -5.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -1.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -4.1542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    0.1208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8625    1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -7.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -6.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -5.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -3.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792    0.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -6.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -6.3000    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
 33 23  1  0
 34 24  1  0
 15 11  1  0
 22 31  2  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA159057

   Methyl 4-[[4-[(4-methoxycarbonylphenyl)carbamothioylamino]phenyl]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: 494.60

Molecular Weight (Monoisotopic): 494.1082

AlogP: 5.32

#Rotatable Bonds: 6

Polar Surface Area: 101.38

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -0.46

CX Basic pKa: 14.95

CX LogP: 8.03

CX LogD: 7.35

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.16

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