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

ID: ALA3100008

Max Phase: Preclinical

Molecular Formula: C21H23FN2O4

Molecular Weight: 386.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(NC(=O)N[C@H]2CC[C@H](Oc3ccc(F)cc3)CC2)cc1

Standard InChI:  InChI=1S/C21H23FN2O4/c1-27-20(25)14-2-6-16(7-3-14)23-21(26)24-17-8-12-19(13-9-17)28-18-10-4-15(22)5-11-18/h2-7,10-11,17,19H,8-9,12-13H2,1H3,(H2,23,24,26)/t17-,19-

Standard InChI Key:  LQCBKHAUABSQEX-UAPYVXQJSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   24.0941  -11.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0930  -12.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8077  -13.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5242  -12.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5214  -11.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8060  -11.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2394  -13.0298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9531  -12.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6683  -13.0275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9518  -11.7912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3820  -12.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0978  -13.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8094  -12.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8125  -11.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0975  -11.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3795  -11.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5278  -11.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2414  -11.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2367  -12.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9495  -13.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6658  -12.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6650  -11.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9517  -11.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3799  -13.0380    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.3795  -11.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3793  -10.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6652  -11.7919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9506  -11.3795    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
  1 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100008

   ---

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: 12.77

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -1.11

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