trans-1-(4-(4-fluorophenoxy)cyclohexyl)-3-(3-(methylthio)phenyl)urea

ID: ALA3100004

PubChem CID: 59168682

Max Phase: Preclinical

Molecular Formula: C20H23FN2O2S

Molecular Weight: 374.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1cccc(NC(=O)N[C@H]2CC[C@H](Oc3ccc(F)cc3)CC2)c1

Standard InChI:  InChI=1S/C20H23FN2O2S/c1-26-19-4-2-3-16(13-19)23-20(24)22-15-7-11-18(12-8-15)25-17-9-5-14(21)6-10-17/h2-6,9-10,13,15,18H,7-8,11-12H2,1H3,(H2,22,23,24)/t15-,18-

Standard InChI Key:  CJBXTXGUKAQNNA-RZDIXWSQSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.0435   -7.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0423   -8.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7571   -8.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4735   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4707   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7553   -6.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1886   -8.6460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9023   -8.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6174   -8.6438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9011   -7.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3312   -8.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0469   -8.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7585   -8.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7615   -7.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0466   -6.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3286   -7.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4768   -7.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1903   -7.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1857   -8.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8984   -8.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6147   -8.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6139   -7.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9006   -7.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3287   -8.6542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.3276   -8.6470    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.6135   -8.2340    0.0000 C   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
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100004

   1-[4-(4-Fluorophenoxy)cyclohexyl]-3-(3-methylsulfanylphenyl)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: 374.48

Molecular Weight (Monoisotopic): 374.1464

AlogP: 5.06

#Rotatable Bonds: 5

Polar Surface Area: 50.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.33

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.59

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