1-(2-fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(2-hydroxy-2-methylpropyl)urea

ID: ALA3809105

PubChem CID: 44511788

Max Phase: Preclinical

Molecular Formula: C26H29F7N4O4

Molecular Weight: 594.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)CNC(=O)Nc1ccc(C(=O)N2CCN(Cc3ccc(C(O)(C(F)(F)F)C(F)(F)F)cc3)CC2)cc1F

Standard InChI:  InChI=1S/C26H29F7N4O4/c1-23(2,40)15-34-22(39)35-20-8-5-17(13-19(20)27)21(38)37-11-9-36(10-12-37)14-16-3-6-18(7-4-16)24(41,25(28,29)30)26(31,32)33/h3-8,13,40-41H,9-12,14-15H2,1-2H3,(H2,34,35,39)

Standard InChI Key:  FQDWDKZDYQQCGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 43  0  0  0  0  0  0  0  0999 V2000
    7.8024    2.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8405    2.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6517  -11.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6404  -10.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -9.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -7.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730   -8.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2625   -9.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417  -10.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355   -9.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -8.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209   -7.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055  -11.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785  -10.3043    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255   -8.5126    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9692   -9.1045    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951  -12.5659    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169  -12.5806    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602  -13.1730    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    1.4978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003    1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990    0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8387    0.8873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  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
  9 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 15 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26  5  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  8 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 38 40  1  0
 40  2  1  0
  2 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3809105

   1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(2-hydroxy-2-methylpropyl)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: 594.53

Molecular Weight (Monoisotopic): 594.2077

AlogP: 3.99

#Rotatable Bonds: 7

Polar Surface Area: 105.14

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.47

CX Basic pKa: 6.51

CX LogP: 2.97

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.36

Np Likeness Score: -1.44

References

1. Stachel SJ, Zerbinatti C, Rudd MT, Cosden M, Suon S, Nanda KK, Wessner K, DiMuzio J, Maxwell J, Wu Z, Uslaner JM, Michener MS, Szczerba P, Brnardic E, Rada V, Kim Y, Meissner R, Wuelfing P, Yuan Y, Ballard J, Holahan M, Klein DJ, Lu J, Fradera X, Parthasarathy G, Uebele VN, Chen Z, Li Y, Li J, Cooke AJ, Bennett DJ, Bilodeau MT, Renger J..  (2016)  Identification and in Vivo Evaluation of Liver X Receptor β-Selective Agonists for the Potential Treatment of Alzheimer's Disease.,  59  (7): [PMID:27011007] [10.1021/acs.jmedchem.6b00176]

Source

Source(1):

• Scientific Literature