N-[1-(5-Chloro-thiophen-2-yl)-2-imidazol-1-yl-ethylidene]-N'-(2,6-dichloro-phenyl)-hydrazine hydrochloride

ID: ALA552561

PubChem CID: 5487569

Max Phase: Preclinical

Molecular Formula: C15H12Cl4N4S

Molecular Weight: 385.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Clc1ccc(/C(Cn2ccnc2)=N\Nc2c(Cl)cccc2Cl)s1

Standard InChI:  InChI=1S/C15H11Cl3N4S.ClH/c16-10-2-1-3-11(17)15(10)21-20-12(8-22-7-6-19-9-22)13-4-5-14(18)23-13;/h1-7,9,21H,8H2;1H/b20-12-;

Standard InChI Key:  ABBHTBYIHZTISS-GRWWMUSUSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   11.5421   -3.1516    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1943   -3.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -3.6304    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5496   -2.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7945   -7.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8001   -1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5445   -6.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -5.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7430   -2.6420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  2  6  2  0
  5  7  1  0
  6  7  1  0
  4  8  1  0
  3 11  2  0
  8 12  2  0
 11 12  1  0
  2 13  1  0
  9 13  1  0
  9 14  1  0
 10 14  2  0
  5 15  2  0
  5 16  1  0
 10 17  1  0
  9 18  1  0
 17 18  2  0
  8 19  1  0
 15 20  1  0
 16 21  1  0
 16 23  2  0
 22 23  1  0
 15 24  1  0
 22 24  2  0
M  END

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: 385.71

Molecular Weight (Monoisotopic): 383.9770

AlogP: 5.42

#Rotatable Bonds: 5

Polar Surface Area: 42.21

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.28

CX Basic pKa: 6.74

CX LogP: 5.32

CX LogD: 5.25

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.47

Np Likeness Score: -1.92

References

1. Dyer RL, Ellames GJ, Hamill BJ, Manley PW, Pope AM..  (1983)  Synthesis of (E)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride, a novel, orally active antifungal agent.,  26  (3): [PMID:6298430] [10.1021/jm00357a023]

Source

Source(1):

• Scientific Literature