(E)-N-(4-methoxyphenyl)-2-(3,4,5-trimethoxybenzylidene)-hydrazinecarbothioamide

ID: ALA4288647

PubChem CID: 9656449

Max Phase: Preclinical

Molecular Formula: C18H21N3O4S

Molecular Weight: 375.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=S)N/N=C/c2cc(OC)c(OC)c(OC)c2)cc1

Standard InChI:  InChI=1S/C18H21N3O4S/c1-22-14-7-5-13(6-8-14)20-18(26)21-19-11-12-9-15(23-2)17(25-4)16(10-12)24-3/h5-11H,1-4H3,(H2,20,21,26)/b19-11+

Standard InChI Key:  DMIIXLSDFKNOKK-YBFXNURJSA-N

Molfile:  

     RDKit          2D

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    1.9001  -26.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086  -26.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3169  -26.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121  -25.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030  -25.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987  -24.2876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042  -23.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999  -23.0581    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141  -24.2801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7196  -23.8678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295  -24.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1350  -23.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8428  -24.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5479  -23.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5440  -23.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292  -22.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270  -23.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103  -27.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035  -27.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8219  -21.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2490  -22.6264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2576  -24.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2615  -25.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2436  -21.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1107  -21.4155    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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  6  1  1  0
  6  7  1  0
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  8  9  2  0
  8 10  1  0
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 16 17  1  0
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  3 19  1  0
 19 20  1  0
 17 21  1  0
 16 22  1  0
 15 23  1  0
 23 24  1  0
 22 25  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4288647

   3,4,5-Trimethoxybenzaldehyde N-(4-methoxyphenyl)thiosemicarbazone

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: 375.45

Molecular Weight (Monoisotopic): 375.1253

AlogP: 3.04

#Rotatable Bonds: 7

Polar Surface Area: 73.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.40

CX Basic pKa: 1.88

CX LogP: 3.28

CX LogD: 3.28

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -1.28

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