1-(3,4-Dicyanophenyl)-3-((1,4-trans)-4-(4-(trifluoromethyl)phenoxy)cyclohexyl)urea

ID: ALA4103285

PubChem CID: 137656748

Max Phase: Preclinical

Molecular Formula: C22H19F3N4O2

Molecular Weight: 428.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(NC(=O)N[C@H]2CC[C@H](Oc3ccc(C(F)(F)F)cc3)CC2)cc1C#N

Standard InChI:  InChI=1S/C22H19F3N4O2/c23-22(24,25)16-2-7-19(8-3-16)31-20-9-5-17(6-10-20)28-21(30)29-18-4-1-14(12-26)15(11-18)13-27/h1-4,7-8,11,17,20H,5-6,9-10H2,(H2,28,29,30)/t17-,20-

Standard InChI Key:  UMOAUOYJELIXPQ-IRJFHVNHSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   36.9868   -7.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9857   -8.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6937   -9.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4034   -8.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4005   -7.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6919   -7.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9086   -7.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9075   -8.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6155   -9.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3252   -8.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3223   -7.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6137   -7.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0285   -7.5176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7377   -7.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4439   -7.5123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7408   -8.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1532   -7.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1539   -8.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8591   -9.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5677   -8.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5665   -7.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8568   -7.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2754   -9.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1067   -7.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8159   -7.9029    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.1036   -6.6798    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.8112   -7.0823    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.6183   -9.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6181  -10.7914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2037   -9.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4956   -9.5679    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
  5 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 28 29  3  0
  9 28  1  0
 30 31  3  0
  8 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103285

   ---

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: 428.41

Molecular Weight (Monoisotopic): 428.1460

AlogP: 4.96

#Rotatable Bonds: 4

Polar Surface Area: 97.94

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.99

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.72

Np Likeness Score: -1.41

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