(E)-2-(4-hydroxy-3-methoxybenzylidene)-N-(naphthalen-1-yl)hydrazinecarbothioamide

ID: ALA4291145

PubChem CID: 145989137

Max Phase: Preclinical

Molecular Formula: C19H17N3O2S

Molecular Weight: 351.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=N/NC(=S)Nc2cccc3ccccc23)ccc1O

Standard InChI:  InChI=1S/C19H17N3O2S/c1-24-18-11-13(9-10-17(18)23)12-20-22-19(25)21-16-8-4-6-14-5-2-3-7-15(14)16/h2-12,23H,1H3,(H2,21,22,25)/b20-12+

Standard InChI Key:  WEBPANOIYHVSFO-UDWIEESQSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.1450   -9.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1439  -10.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8519  -10.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8501   -8.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5587   -9.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5595  -10.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2680  -10.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9763  -10.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9716   -9.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2625   -8.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2581   -8.1749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9637   -7.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9593   -6.9454    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6735   -8.1674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3791   -7.7551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0889   -8.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7945   -7.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5023   -8.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2073   -7.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2034   -6.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4886   -6.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7865   -6.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4814   -5.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1854   -5.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9084   -6.5137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 21 23  1  0
 23 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4291145

   ---

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: 351.43

Molecular Weight (Monoisotopic): 351.1041

AlogP: 3.87

#Rotatable Bonds: 4

Polar Surface Area: 65.88

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.59

CX Basic pKa: 2.36

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.38

Np Likeness Score: -1.21

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