trans-1-(4-(2-Fluorophenoxy)cyclohexyl)-3-(3-(trifluoromethyl)-phenyl)urea

ID: ALA3100012

PubChem CID: 72793024

Max Phase: Preclinical

Molecular Formula: C20H20F4N2O2

Molecular Weight: 396.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(C(F)(F)F)c1)N[C@H]1CC[C@H](Oc2ccccc2F)CC1

Standard InChI:  InChI=1S/C20H20F4N2O2/c21-17-6-1-2-7-18(17)28-16-10-8-14(9-11-16)25-19(27)26-15-5-3-4-13(12-15)20(22,23)24/h1-7,12,14,16H,8-11H2,(H2,25,26,27)/t14-,16-

Standard InChI Key:  LIWYOVAGDQLRPS-KOMQPUFPSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.2611   -7.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599   -8.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747   -8.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6911   -8.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883   -7.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9729   -7.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -7.2936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172   -7.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8301   -7.2882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1203   -8.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -7.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5469   -8.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2587   -8.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9741   -8.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9730   -7.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2565   -7.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6885   -8.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4030   -8.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1146   -8.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8286   -8.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8291   -7.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1096   -7.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986   -7.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -9.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600  -10.1899    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889  -10.1902    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666  -10.5999    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1135   -9.7620    0.0000 F   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
  5  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
  3 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 19 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100012

   1-[4-(2-Fluorophenoxy)cyclohexyl]-3-[3-(trifluoromethyl)phenyl]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: 396.38

Molecular Weight (Monoisotopic): 396.1461

AlogP: 5.36

#Rotatable Bonds: 4

Polar Surface Area: 50.36

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.30

CX Basic pKa: ┄

CX LogP: 4.87

CX LogD: 4.87

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.52

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