(E)-2-(3,4-dimethoxybenzylidene)-N-(4-methoxyphenyl)hydrazinecarbothioamide

ID: ALA4289736

PubChem CID: 9629751

Max Phase: Preclinical

Molecular Formula: C17H19N3O3S

Molecular Weight: 345.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=S)N/N=C/c2ccc(OC)c(OC)c2)cc1

Standard InChI:  InChI=1S/C17H19N3O3S/c1-21-14-7-5-13(6-8-14)19-17(24)20-18-11-12-4-9-15(22-2)16(10-12)23-3/h4-11H,1-3H3,(H2,19,20,24)/b18-11+

Standard InChI Key:  GCGUMCKVRBXPNY-WOJGMQOQSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.4470   -6.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -7.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1563   -8.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8646   -7.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8599   -6.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1508   -6.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -5.6367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8520   -5.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476   -4.4071    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5618   -5.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2673   -5.2168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9772   -5.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6827   -5.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3906   -5.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0956   -5.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0917   -4.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769   -3.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6747   -4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -8.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -9.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3697   -3.1669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7967   -3.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5071   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6584   -2.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  3 19  1  0
 19 20  1  0
 17 21  1  0
 16 22  1  0
 22 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4289736

   3,4-dimethoxybenzaldehyde N-(4-methoxyphenyl)thiosemicarbazone

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: 345.42

Molecular Weight (Monoisotopic): 345.1147

AlogP: 3.03

#Rotatable Bonds: 6

Polar Surface Area: 64.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.41

CX Basic pKa: 2.07

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.48

Np Likeness Score: -1.51

References

1. Sens L, de Souza ACA, Pacheco LA, Menegatti ACO, Mori M, Mascarello A, Nunes RJ, Terenzi H..  (2018)  Synthetic thiosemicarbazones as a new class of Mycobacterium tuberculosis protein tyrosine phosphatase A inhibitors.,  26  (21): [PMID:30389409] [10.1016/j.bmc.2018.10.030]

Source

Source(1):

• Scientific Literature