3-(5,6-Dichloro-2-methyl-1H-benzimidazol-1-yl)-N'-[(E)-(2-hydroxynaphthalen-1-yl)methylidene]propanehydrazide

ID: ALA2431387

PubChem CID: 136260538

Max Phase: Preclinical

Molecular Formula: C22H18Cl2N4O2

Molecular Weight: 441.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2cc(Cl)c(Cl)cc2n1CCC(=O)N/N=C/c1c(O)ccc2ccccc12

Standard InChI:  InChI=1S/C22H18Cl2N4O2/c1-13-26-19-10-17(23)18(24)11-20(19)28(13)9-8-22(30)27-25-12-16-15-5-3-2-4-14(15)6-7-21(16)29/h2-7,10-12,29H,8-9H2,1H3,(H,27,30)/b25-12+

Standard InChI Key:  ZVZXHOAILXWYIN-BRJLIKDPSA-N

Molfile:  

     RDKit          2D

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    3.8011  -11.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5248  -11.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620  -12.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059  -11.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448  -11.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730  -12.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341  -12.9094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2129  -12.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678  -11.6463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9862  -12.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5160  -13.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2189  -14.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1999  -14.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020  -15.4064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787  -15.3734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830  -16.2275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5851  -16.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5660  -17.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8421  -17.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8227  -18.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5253  -19.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2648  -17.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2471  -18.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9442  -19.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6552  -18.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6732  -17.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9755  -17.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447  -17.4449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694  -10.5426    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7216  -12.0909    0.0000 Cl  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  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 23  1  0
 22 18  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
 19 28  1  0
  1 29  1  0
  2 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2431387

   ---

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: 441.32

Molecular Weight (Monoisotopic): 440.0807

AlogP: 5.05

#Rotatable Bonds: 5

Polar Surface Area: 79.51

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.57

CX Basic pKa: 6.03

CX LogP: 4.55

CX LogD: 4.50

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -1.64

References

1. Zhou M, Eun YJ, Guzei IA, Weibel DB..  (2013)  Structure-activity studies of divin: an inhibitor of bacterial cell division.,  4  (9): [PMID:24044050] [10.1021/ml400234x]

Source

Source(1):

• Scientific Literature