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

ID: ALA3100022

PubChem CID: 59168730

Max Phase: Preclinical

Molecular Formula: C19H20ClFN2O2

Molecular Weight: 362.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(Cl)c1)N[C@H]1CC[C@H](Oc2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C19H20ClFN2O2/c20-13-2-1-3-16(12-13)23-19(24)22-15-6-10-18(11-7-15)25-17-8-4-14(21)5-9-17/h1-5,8-9,12,15,18H,6-7,10-11H2,(H2,22,23,24)/t15-,18-

Standard InChI Key:  XLAGKZXEQHSLPW-RZDIXWSQSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.9770   -4.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9758   -5.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6906   -6.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4070   -5.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4041   -4.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6888   -4.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1221   -6.1212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8358   -5.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5509   -6.1189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8346   -4.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2647   -5.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9803   -6.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6919   -5.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6950   -4.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9800   -4.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2621   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4103   -4.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1238   -4.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1192   -5.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8319   -6.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5482   -5.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5474   -4.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8341   -4.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2622   -6.1293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.2611   -6.1222    0.0000 Cl  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
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100022

   1-(3-Chlorophenyl)-3-[4-(4-fluorophenoxy)cyclohexyl]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: 362.83

Molecular Weight (Monoisotopic): 362.1197

AlogP: 4.99

#Rotatable Bonds: 4

Polar Surface Area: 50.36

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.23

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.80

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