1-{2-[2-Hydroxy-3-(4-hydroxy-4-phenyl-piperidin-1-yl)-propoxy]-phenyl}-3-phenyl-propan-1-one

ID: ALA344278

PubChem CID: 9981658

Max Phase: Preclinical

Molecular Formula: C29H33NO4

Molecular Weight: 459.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccccc1)c1ccccc1OCC(O)CN1CCC(O)(c2ccccc2)CC1

Standard InChI:  InChI=1S/C29H33NO4/c31-25(21-30-19-17-29(33,18-20-30)24-11-5-2-6-12-24)22-34-28-14-8-7-13-26(28)27(32)16-15-23-9-3-1-4-10-23/h1-14,25,31,33H,15-22H2

Standard InChI Key:  YQLGIKXRTZJNLK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    7.6292    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -0.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0375    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417    0.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    0.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542    1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2667    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167    2.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3 12  1  0
  4  2  1  0
  5  1  1  0
  6  1  1  0
  7  8  1  0
  8 16  1  0
  9  1  1  0
 10  4  2  0
 11  4  1  0
 12  6  1  0
 13  5  1  0
 14  3  1  0
 15 14  1  0
 16 15  1  0
 17  1  1  0
 18 11  1  0
 19 15  1  0
 20 18  1  0
 21  2  2  0
 22  7  2  0
 23  9  2  0
 24  9  1  0
 25 20  1  0
 26 20  2  0
 27 30  2  0
 28 23  1  0
 29 24  2  0
 30 22  1  0
 31 26  1  0
 32 25  2  0
 33 31  2  0
 34 29  1  0
 13  3  1  0
 34 28  2  0
 21 27  1  0
 33 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA344278

   1-(2-(2-Hydroxy-3-(4-hydroxy-4-phenylpiperidin-1-yl)propoxy)phenyl)-3-phenylpropan-1-one

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: 459.59

Molecular Weight (Monoisotopic): 459.2410

AlogP: 4.23

#Rotatable Bonds: 10

Polar Surface Area: 70.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.74

CX Basic pKa: 7.43

CX LogP: 4.01

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -0.38

References

1. Fleischer R, Wiese M..  (2003)  Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.,  46  (23): [PMID:14584949] [10.1021/jm030876r]

2. Kaiser D, Terfloth L, Kopp S, Schulz J, de Laet R, Chiba P, Ecker GF, Gasteiger J..  (2007)  Self-organizing maps for identification of new inhibitors of P-glycoprotein.,  50  (7): [PMID:17352460] [10.1021/jm060604z]

3. Jabeen I, Pleban K, Rinner U, Chiba P, Ecker GF..  (2012)  Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein.,  55  (7): [PMID:22452412] [10.1021/jm201705f]

Source

Source(1):

• Scientific Literature