(E)-2-(4-(dimethylamino)benzylidene)-N-(naphthalen-1-yl)hydrazinecarbothioamide

ID: ALA4289164

PubChem CID: 15758485

Max Phase: Preclinical

Molecular Formula: C20H20N4S

Molecular Weight: 348.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(/C=N/NC(=S)Nc2cccc3ccccc23)cc1

Standard InChI:  InChI=1S/C20H20N4S/c1-24(2)17-12-10-15(11-13-17)14-21-23-20(25)22-19-9-5-7-16-6-3-4-8-18(16)19/h3-14H,1-2H3,(H2,22,23,25)/b21-14+

Standard InChI Key:  OPQWHMIFPOOJNN-KGENOOAVSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   10.4485  -22.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4472  -23.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1621  -23.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1603  -22.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8756  -22.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8765  -23.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5917  -23.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3068  -23.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3019  -22.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861  -22.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5817  -21.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2940  -20.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2896  -20.0907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.0106  -21.3244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7229  -20.9080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4395  -21.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1518  -20.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8663  -21.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5782  -20.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5742  -20.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8525  -19.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1437  -20.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2859  -19.6548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0031  -20.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2805  -18.8298    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
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4289164

   1-[(E)-[4-(dimethylamino)phenyl]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: 348.48

Molecular Weight (Monoisotopic): 348.1409

AlogP: 4.23

#Rotatable Bonds: 4

Polar Surface Area: 39.66

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: 4.58

CX LogP: 5.00

CX LogD: 5.00

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: -1.88

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