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

ID: ALA148260

PubChem CID: 10836448

Max Phase: Preclinical

Molecular Formula: C27H29NO4

Molecular Weight: 431.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccccc1)c1ccccc1OCC(O)CN1CCC(O)(c2ccccc2)CC1

Standard InChI:  InChI=1S/C27H29NO4/c29-23(19-28-17-15-27(31,16-18-28)22-11-5-2-6-12-22)20-32-25-14-8-7-13-24(25)26(30)21-9-3-1-4-10-21/h1-14,23,29,31H,15-20H2

Standard InChI Key:  KNWQIFLHCZAXAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.6667   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -0.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625   -0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9500    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -1.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -0.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0667    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9500   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750   -0.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9500   -0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0917   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8917    0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6500    1.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3000    1.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500    2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8792    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4 14  1  0
  5 13  1  0
  6 12  1  0
  7  1  1  0
  8  2  2  0
  9  7  1  0
 10  2  1  0
 11  3  1  0
 12  4  1  0
 13  4  1  0
 14 15  1  0
 15 16  1  0
 16  9  1  0
 17  3  1  0
 18  1  2  0
 19 15  1  0
 20  7  2  0
 21 10  2  0
 22 10  1  0
 23 11  2  0
 24 11  1  0
 25 18  1  0
 26 22  2  0
 27 25  2  0
 28 23  1  0
 29 24  2  0
 30 21  1  0
 31 26  1  0
 32 29  1  0
 27 20  1  0
 31 30  2  0
  6  3  1  0
 32 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA148260

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

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: 431.53

Molecular Weight (Monoisotopic): 431.2097

AlogP: 3.64

#Rotatable Bonds: 8

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: 3.63

CX LogD: 3.31

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: -0.55

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