(E)-2-([1,1'-biphenyl]-4-ylmethylene)-N-(4-methoxyphenyl)-hydrazinecarbothioamide

ID: ALA4291222

PubChem CID: 9715006

Max Phase: Preclinical

Molecular Formula: C21H19N3OS

Molecular Weight: 361.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=S)N/N=C/c2ccc(-c3ccccc3)cc2)cc1

Standard InChI:  InChI=1S/C21H19N3OS/c1-25-20-13-11-19(12-14-20)23-21(26)24-22-15-16-7-9-18(10-8-16)17-5-3-2-4-6-17/h2-15H,1H3,(H2,23,24,26)/b22-15+

Standard InChI Key:  IMCCYPMIEKKUMP-PXLXIMEGSA-N

Molfile:  

     RDKit          2D

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   28.4629  -17.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1715  -17.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8797  -17.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8750  -16.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1659  -16.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1616  -15.4636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8671  -15.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8627  -14.2341    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.5769  -15.4561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2825  -15.0437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9923  -15.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6979  -15.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4057  -15.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1107  -15.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1068  -14.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3920  -13.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6899  -14.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1732  -18.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4663  -19.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8110  -13.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5217  -14.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2262  -13.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2212  -12.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5058  -12.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8043  -12.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  4  5  1  0
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  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
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  3 19  1  0
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 21 22  2  0
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 16 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4291222

   1-(4-methoxyphenyl)-3-[(E)-(4-phenylphenyl)methylideneamino]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: 361.47

Molecular Weight (Monoisotopic): 361.1249

AlogP: 4.68

#Rotatable Bonds: 5

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: 11.41

CX Basic pKa: 2.57

CX LogP: 5.40

CX LogD: 5.40

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.39

Np Likeness Score: -1.54

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