trans-1-(4-(4-fluorophenoxy)cyclohexyl)-3-(4-nitrophenyl)urea

ID: ALA3100002

PubChem CID: 68539441

Max Phase: Preclinical

Molecular Formula: C19H20FN3O4

Molecular Weight: 373.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc([N+](=O)[O-])cc1)N[C@H]1CC[C@H](Oc2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C19H20FN3O4/c20-13-1-9-17(10-2-13)27-18-11-5-15(6-12-18)22-19(24)21-14-3-7-16(8-4-14)23(25)26/h1-4,7-10,15,18H,5-6,11-12H2,(H2,21,22,24)/t15-,18-

Standard InChI Key:  GYTOVXSJLMFOHX-RZDIXWSQSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   22.7936   -2.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7925   -3.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5073   -3.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2237   -3.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2209   -2.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5055   -1.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9389   -3.4464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6526   -3.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3677   -3.4442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6513   -2.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0815   -3.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7972   -3.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5088   -3.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5119   -2.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7969   -1.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0789   -2.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2272   -1.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9407   -2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9361   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6488   -3.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3652   -3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3644   -2.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6510   -1.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0792   -3.4546    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.0807   -1.8001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3664   -2.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0805   -0.9751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 11  9  1  6
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  1
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 25 26  2  0
 25 27  1  0
  1 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3100002

   1-[4-(4-Fluorophenoxy)cyclohexyl]-3-(4-nitrophenyl)urea

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: 373.38

Molecular Weight (Monoisotopic): 373.1438

AlogP: 4.25

#Rotatable Bonds: 5

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: 12.45

CX Basic pKa: ┄

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -1.51

References

1. Chen T, Takrouri K, Hee-Hwang S, Rana S, Yefidoff-Freedman R, Halperin J, Natarajan A, Morisseau C, Hammock B, Chorev M, Aktas BH..  (2013)  Explorations of substituted urea functionality for the discovery of new activators of the heme-regulated inhibitor kinase.,  56  (23): [PMID:24261904] [10.1021/jm400793v]

Source

Source(1):

• Scientific Literature