cis-Methyl 2-(3-(4-(4-fluorophenoxy)cyclohexyl)ureido)benzoate

ID: ALA3100006

PubChem CID: 72793022

Max Phase: Preclinical

Molecular Formula: C21H23FN2O4

Molecular Weight: 386.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccccc1NC(=O)N[C@H]1CC[C@@H](Oc2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C21H23FN2O4/c1-27-20(25)18-4-2-3-5-19(18)24-21(26)23-15-8-12-17(13-9-15)28-16-10-6-14(22)7-11-16/h2-7,10-11,15,17H,8-9,12-13H2,1H3,(H2,23,24,26)/t15-,17+

Standard InChI Key:  BUGLXIOTHISLCJ-WOVMCDHWSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.9484   -3.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473   -4.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6621   -4.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -4.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -3.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6603   -3.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6619   -5.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473   -6.0441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762   -6.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0936   -4.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8074   -4.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -4.8026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8061   -3.5662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2363   -4.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9520   -4.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6637   -4.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6666   -3.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9517   -3.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2338   -3.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3820   -3.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0955   -3.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0910   -4.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8037   -4.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5200   -4.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5192   -3.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8059   -3.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2341   -4.8130    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330   -5.6314    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
  3  7  1  0
  7  8  1  0
  7  9  2  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 14 12  1  6
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  6
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
  8 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100006

   Methyl 2-[[4-(4-fluorophenoxy)cyclohexyl]carbamoylamino]benzoate

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: 12.32

CX Basic pKa: ┄

CX LogP: 4.64

CX LogD: 4.64

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