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

ID: ALA3100013

PubChem CID: 72793088

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](Oc2cccc(F)c2)CC1

Standard InChI:  InChI=1S/C20H20F4N2O2/c21-14-4-2-6-18(12-14)28-17-9-7-15(8-10-17)25-19(27)26-16-5-1-3-13(11-16)20(22,23)24/h1-6,11-12,15,17H,7-10H2,(H2,25,26,27)/t15-,17-

Standard InChI Key:  AXRKHRWOKDMGKA-JCNLHEQBSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   13.5982   -7.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5970   -8.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3119   -8.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0282   -8.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0254   -7.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3101   -7.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7383   -7.2392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4543   -7.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1672   -7.2339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4574   -8.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8832   -7.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8840   -8.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5958   -8.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3112   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3101   -7.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5936   -7.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0256   -8.8823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7401   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4517   -8.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1656   -8.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1661   -7.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4466   -7.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7356   -7.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3117   -9.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5970  -10.1356    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0260  -10.1360    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3038  -10.5455    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8799   -8.8838    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
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100013

   1-[4-(3-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: -1.58

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