1-((1,4-trans)-4-(4-Cyanophenoxy)cyclohexyl)-3-(3-(trifluoromethyl)phenyl)urea

ID: ALA4072326

PubChem CID: 117954420

Max Phase: Preclinical

Molecular Formula: C21H20F3N3O2

Molecular Weight: 403.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(O[C@H]2CC[C@H](NC(=O)Nc3cccc(C(F)(F)F)c3)CC2)cc1

Standard InChI:  InChI=1S/C21H20F3N3O2/c22-21(23,24)15-2-1-3-17(12-15)27-20(28)26-16-6-10-19(11-7-16)29-18-8-4-14(13-25)5-9-18/h1-5,8-9,12,16,19H,6-7,10-11H2,(H2,26,27,28)/t16-,19-

Standard InChI Key:  PZUCVHKVJAOZFX-RUCARUNLSA-N

Molfile:  

     RDKit          2D

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   34.7829   -8.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7817   -9.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4898   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1994   -9.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1966   -8.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4880   -7.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7047   -8.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7035   -9.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4116   -9.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1212   -9.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1184   -8.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4098   -7.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8246   -7.9923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5338   -8.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2400   -7.9869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5369   -9.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9492   -8.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9500   -9.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6551   -9.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3637   -9.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3626   -8.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6529   -7.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0714   -9.6153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4114  -10.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7036  -10.8612    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.1190  -10.8616    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.4036  -11.2673    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.9005   -7.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6067   -7.5592    0.0000 N   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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 17 15  1  6
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  1
 23  2  1  0
  9 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 28 29  3  0
  5 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072326

   1-[4-(4-Cyanophenoxy)cyclohexyl]-3-[3-(trifluoromethyl)phenyl]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: 403.40

Molecular Weight (Monoisotopic): 403.1508

AlogP: 5.09

#Rotatable Bonds: 4

Polar Surface Area: 74.15

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.30

CX Basic pKa: ┄

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: -1.56

References

1. Yefidoff-Freedman R, Fan J, Yan L, Zhang Q, Dos Santos GRR, Rana S, Contreras JI, Sahoo R, Wan D, Young J, Dias Teixeira KL, Morisseau C, Halperin J, Hammock B, Natarajan A, Wang P, Chorev M, Aktas BH..  (2017)  Development of 1-((1,4-trans)-4-Aryloxycyclohexyl)-3-arylurea Activators of Heme-Regulated Inhibitor as Selective Activators of the Eukaryotic Initiation Factor 2 Alpha (eIF2α) Phosphorylation Arm of the Integrated Endoplasmic Reticulum Stress Response.,  60  (13): [PMID:28590739] [10.1021/acs.jmedchem.7b00059]

Source

Source(1):

• Scientific Literature