1-[3-(2-Hydroxy-3-piperidin-1-yl-propoxy)-phenyl]-3-phenyl-propan-1-one

ID: ALA146135

PubChem CID: 11428594

Max Phase: Preclinical

Molecular Formula: C23H29NO3

Molecular Weight: 367.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccccc1)c1cccc(OCC(O)CN2CCCCC2)c1

Standard InChI:  InChI=1S/C23H29NO3/c25-21(17-24-14-5-2-6-15-24)18-27-22-11-7-10-20(16-22)23(26)13-12-19-8-3-1-4-9-19/h1,3-4,7-11,16,21,25H,2,5-6,12-15,17-18H2

Standard InChI Key:  HIWSPAOYMSSPJM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    7.9792    0.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    0.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417    1.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4042    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4042    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4 10  1  0
  5  2  2  0
  6  2  1  0
  7  1  1  0
  8 11  1  0
  9  7  1  0
 10  8  1  0
 11  9  1  0
 12  6  1  0
 13  9  1  0
 14 12  1  0
 15  1  1  0
 16  1  1  0
 17 18  2  0
 18 19  1  0
 19 10  2  0
 20 14  2  0
 21 14  1  0
 22 16  1  0
 23 15  1  0
 24 21  2  0
 25 20  1  0
 26 22  1  0
 27 24  1  0
 23 26  1  0
  3 17  1  0
 27 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA146135

   1-(3-(2-Hydroxy-3-(piperidin-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: 367.49

Molecular Weight (Monoisotopic): 367.2147

AlogP: 3.73

#Rotatable Bonds: 9

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.04

CX LogP: 3.89

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.80

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]

Source

Source(1):

• Scientific Literature