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

ID: ALA3764996

PubChem CID: 127041494

Max Phase: Preclinical

Molecular Formula: C21H16Cl2N2O3

Molecular Weight: 415.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)Oc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H16Cl2N2O3/c22-15-6-9-17(10-7-15)25-20(26)18-12-16(23)8-11-19(18)28-21(27)24-13-14-4-2-1-3-5-14/h1-12H,13H2,(H,24,27)(H,25,26)

Standard InChI Key:  YFEVQIYXPKSBAM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.8933   -3.7570    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
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    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
   -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
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -8.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -6.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -5.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913   -8.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934   -9.7649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -7.6659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952  -10.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952  -12.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962  -12.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0029  -12.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0029  -10.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961   -9.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421  -12.6181    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8268   -8.1110    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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  2  5  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 18 19  1  0
 18 20  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 24 27  1  0
 19 21  1  0
 13 18  1  0
 15 28  1  0
  4 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3764996

   ---

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: 415.28

Molecular Weight (Monoisotopic): 414.0538

AlogP: 5.53

#Rotatable Bonds: 5

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: 5.50

CX LogD: 5.50

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.35

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