(E)-2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-p-tolylhydrazinecarbothioamide

ID: ALA4290444

PubChem CID: 6875628

Max Phase: Preclinical

Molecular Formula: C16H15N3O2S

Molecular Weight: 313.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=S)N/N=C/c2ccc3c(c2)OCO3)cc1

Standard InChI:  InChI=1S/C16H15N3O2S/c1-11-2-5-13(6-3-11)18-16(22)19-17-9-12-4-7-14-15(8-12)21-10-20-14/h2-9H,10H2,1H3,(H2,18,19,22)/b17-9+

Standard InChI Key:  ZMRFYGWNINETGN-RQZCQDPDSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   15.2757  -28.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2764  -28.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9891  -29.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974  -28.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6926  -28.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9835  -27.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9792  -26.8011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6847  -26.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6804  -25.5633    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.3987  -26.7936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1084  -26.3771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8224  -26.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5320  -26.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2440  -26.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2303  -25.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5240  -25.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9908  -30.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9492  -25.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9556  -26.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7362  -26.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2098  -25.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7259  -25.2872    0.0000 O   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 19  1  0
 18 15  1  0
 15 16  2  0
 16 13  1  0
  3 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4290444

   1-[(E)-1,3-benzodioxol-5-ylmethylideneamino]-3-(4-methylphenyl)thiourea

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: 313.38

Molecular Weight (Monoisotopic): 313.0885

AlogP: 3.04

#Rotatable Bonds: 3

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.41

CX Basic pKa: 2.11

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.52

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