trans-methyl 3-(3-(4-(4-fluorophenoxy)cyclohexyl)ureido)benzoate

ID: ALA3100007

Max Phase: Preclinical

Molecular Formula: C21H23FN2O4

Molecular Weight: 386.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cccc(NC(=O)N[C@H]2CC[C@H](Oc3ccc(F)cc3)CC2)c1

Standard InChI:  InChI=1S/C21H23FN2O4/c1-27-20(25)14-3-2-4-17(13-14)24-21(26)23-16-7-11-19(12-8-16)28-18-9-5-15(22)6-10-18/h2-6,9-10,13,16,19H,7-8,11-12H2,1H3,(H2,23,24,26)/t16-,19-

Standard InChI Key:  SAWRONONHYMMHU-RUCARUNLSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   12.6357  -11.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6345  -12.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3493  -12.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0657  -12.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0629  -11.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3475  -11.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7808  -12.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4946  -12.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2097  -12.7189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4934  -11.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9235  -12.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6392  -12.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3508  -12.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3538  -11.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6389  -11.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9209  -11.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0692  -11.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7827  -11.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7781  -12.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4908  -12.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2072  -12.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2063  -11.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4930  -11.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9212  -12.7293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9197  -12.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2056  -12.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9190  -13.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6332  -13.9602    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  2  0
 25 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100007

   ---

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: 386.42

Molecular Weight (Monoisotopic): 386.1642

AlogP: 4.12

#Rotatable Bonds: 5

Polar Surface Area: 76.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -1.24

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