1-(2-(benzyloxy)phenyl)-3-(4-nitrophenyl)urea

ID: ALA5268140

Max Phase: Preclinical

Molecular Formula: C20H17N3O4

Molecular Weight: 363.37

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccccc1OCc1ccccc1

Standard InChI:  InChI=1S/C20H17N3O4/c24-20(21-16-10-12-17(13-11-16)23(25)26)22-18-8-4-5-9-19(18)27-14-15-6-2-1-3-7-15/h1-13H,14H2,(H2,21,22,24)

Standard InChI Key:  PFTUFEGNDHCJDG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
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   -0.7121    0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121    1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235   -0.4088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1349   -0.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1349   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235   -2.0517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -0.8196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -2.0517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -1.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205   -0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106   -0.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8434   -0.4108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8434    0.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5548   -0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8418   -2.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -0.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  7  2  1  0
  8  7  1  0
  9  8  1  0
 10  9  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  2  0
 21 18  1  0
 21 22  2  0
 21 23  1  0
 24 10  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
  9 27  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5268140

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 363.37

Molecular Weight (Monoisotopic): 363.1219

AlogP: 4.82

#Rotatable Bonds: 6

Polar Surface Area: 93.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.59

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -1.65

References

1. Dunyak BM, Gestwicki JE..  (2016)  Peptidyl-Proline Isomerases (PPIases): Targets for Natural Products and Natural Product-Inspired Compounds.,  59  (21): [PMID:27409354] [10.1021/acs.jmedchem.6b00411]

Source

Source(1):

• Scientific Literature