(E)-2-(4-methoxybenzylidene)-N-(naphthalen-1-yl)hydrazine-carbothioamide

ID: ALA4288832

PubChem CID: 10065544

Max Phase: Preclinical

Molecular Formula: C19H17N3OS

Molecular Weight: 335.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=N/NC(=S)Nc2cccc3ccccc23)cc1

Standard InChI:  InChI=1S/C19H17N3OS/c1-23-16-11-9-14(10-12-16)13-20-22-19(24)21-18-8-4-6-15-5-2-3-7-17(15)18/h2-13H,1H3,(H2,21,22,24)/b20-13+

Standard InChI Key:  NUSBAKWKTHOATC-DEDYPNTBSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   22.7479   -3.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7467   -4.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4548   -4.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4530   -3.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1616   -3.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1624   -4.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8709   -4.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5792   -4.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5744   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8653   -3.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8610   -2.2069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5665   -1.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5622   -0.9774    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.2764   -2.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9819   -1.7871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6918   -2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3973   -1.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1051   -2.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8102   -1.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8063   -0.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0914   -0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3893   -0.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5113   -0.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2217   -0.9496    0.0000 C   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
 20 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4288832

   1-[(E)-(4-methoxyphenyl)methylideneamino]-3-naphthalen-1-ylthiourea

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: 335.43

Molecular Weight (Monoisotopic): 335.1092

AlogP: 4.17

#Rotatable Bonds: 4

Polar Surface Area: 45.65

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.40

CX Basic pKa: 2.64

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.43

Np Likeness Score: -1.66

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