1-(3,5-Bis(trifluoromethyl)phenyl)-3-((1,4-trans)-4-(4-(trifluoromethyl)phenoxy)cyclohexyl)urea

ID: ALA4095536

PubChem CID: 117954770

Max Phase: Preclinical

Molecular Formula: C22H19F9N2O2

Molecular Weight: 514.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N[C@H]1CC[C@H](Oc2ccc(C(F)(F)F)cc2)CC1

Standard InChI:  InChI=1S/C22H19F9N2O2/c23-20(24,25)12-1-5-17(6-2-12)35-18-7-3-15(4-8-18)32-19(34)33-16-10-13(21(26,27)28)9-14(11-16)22(29,30)31/h1-2,5-6,9-11,15,18H,3-4,7-8H2,(H2,32,33,34)/t15-,18-

Standard InChI Key:  MGYQQVMSZRZRGX-RZDIXWSQSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   23.2308  -19.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2296  -20.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9377  -21.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6473  -20.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6445  -19.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9359  -19.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1526  -19.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1514  -20.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8595  -21.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5691  -20.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5663  -19.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8577  -19.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2725  -19.4825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9817  -19.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6879  -19.4771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9848  -20.7056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3971  -19.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3978  -20.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1030  -21.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8116  -20.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8105  -19.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1008  -19.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5193  -21.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3506  -19.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0599  -19.8678    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.3476  -18.6447    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.0552  -19.0472    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.8593  -21.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1514  -22.3514    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.5669  -22.3518    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.8515  -22.7575    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.4447  -19.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4446  -18.6717    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7371  -19.8977    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7342  -19.0802    0.0000 F   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
  9 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  7 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095536

   1-[3,5-Bis(trifluoromethyl)phenyl]-3-[4-[4-(trifluoromethyl)phenoxy]cyclohexyl]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: 514.39

Molecular Weight (Monoisotopic): 514.1303

AlogP: 7.25

#Rotatable Bonds: 4

Polar Surface Area: 50.36

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.06

CX Basic pKa: ┄

CX LogP: 6.48

CX LogD: 6.48

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.42

Np Likeness Score: -0.96

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