4-Chloro-2-[(4-chlorophenyl)carbamoyl]phenyl cyclohexylcarbamate

ID: ALA3763304

PubChem CID: 127028068

Max Phase: Preclinical

Molecular Formula: C20H20Cl2N2O3

Molecular Weight: 407.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCCCC1)Oc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H20Cl2N2O3/c21-13-6-9-16(10-7-13)23-19(25)17-12-14(22)8-11-18(17)27-20(26)24-15-4-2-1-3-5-15/h6-12,15H,1-5H2,(H,23,25)(H,24,26)

Standard InChI Key:  RDWJZBHFYQILCP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.5951   -3.0039    0.0000 C   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
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 O   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
   -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
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876   -6.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1824   -7.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -8.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844   -7.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895   -6.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -5.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -6.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4978   -4.0692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0915   -5.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879   -6.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6896   -5.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6949   -3.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3985   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0968   -3.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7362   -3.1956    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8767   -9.4579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 10  1  0
  2  5  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  1  0
 17 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 23 26  1  0
 18 20  1  0
 12 17  1  0
 14 27  1  0
  4 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3763304

   ---

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: 407.30

Molecular Weight (Monoisotopic): 406.0851

AlogP: 5.67

#Rotatable Bonds: 4

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.57

CX LogD: 5.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.33

References

1. Krátký M, Vinšová J..  (2016)  Salicylanilide N-monosubstituted carbamates: Synthesis and in vitro antimicrobial activity.,  24  (6): [PMID:26879856] [10.1016/j.bmc.2016.02.004]

2. Krátký M, Janďourek O, Baranyai Z, Novotná E, Stolaříková J, Bősze S, Vinšová J..  (2019)  Phenolic N-monosubstituted carbamates: Antitubercular and toxicity evaluation of multi-targeting compounds.,  181  [PMID:31401536] [10.1016/j.ejmech.2019.111578]

Source

Source(1):

• Scientific Literature