4-(4-(((2s,5s)-2-((1H-imidazol-1-yl)methyl)-2-(2-chlorophenyl)-1,3-dioxan-5-yloxy)methyl)phenyl)morpholine

ID: ALA4286761

Max Phase: Preclinical

Molecular Formula: C25H28ClN3O4

Molecular Weight: 469.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccccc1[C@]1(Cn2ccnc2)OC[C@@H](OCc2ccc(N3CCOCC3)cc2)CO1

Standard InChI:  InChI=1S/C25H28ClN3O4/c26-24-4-2-1-3-23(24)25(18-28-10-9-27-19-28)32-16-22(17-33-25)31-15-20-5-7-21(8-6-20)29-11-13-30-14-12-29/h1-10,19,22H,11-18H2/t22-,25-

Standard InChI Key:  MOERNEWHDHHREB-RZFKFIIISA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   43.4268   -5.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4256   -5.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1405   -6.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8568   -5.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8540   -5.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1386   -4.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7130   -4.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7148   -3.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.0043   -3.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2875   -3.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2857   -4.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0007   -5.0972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7074   -5.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9901   -5.9159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.2374   -5.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6813   -6.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0889   -6.9071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.8971   -6.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5746   -3.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8586   -3.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1456   -3.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1519   -2.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4398   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7229   -2.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7226   -3.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4354   -3.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0094   -2.1905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0152   -1.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3058   -0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5880   -1.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5842   -2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2982   -2.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1362   -3.8579    0.0000 Cl  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  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  1  7  1  0
  7 13  1  1
 13 14  1  0
 17 18  2  0
 15 16  2  0
 14 15  1  0
 16 17  1  0
 18 14  1  0
 10 19  1  1
 19 20  1  0
 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
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
  6 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4286761

   ---

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: 469.97

Molecular Weight (Monoisotopic): 469.1768

AlogP: 3.86

#Rotatable Bonds: 7

Polar Surface Area: 57.98

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.42

CX LogP: 4.33

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -0.78

References

1.  (2016)  Novel functionalized 5-(phenoxymethyl)-1,3-dioxane analogs exhibiting cytochrome p450 inhibition and their method of use, 

2. Blass, Benjamin E BE and 18 more authors.  2016-12-01  Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.  [PMID:27789139]

3. Fehl, Charlie C and 5 more authors.  2018-06-14  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.  [PMID:29792703]

Source

Source(1):

• Patent Bioactivity Data