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

ID: ALA149234

PubChem CID: 9976755

Max Phase: Preclinical

Molecular Formula: C24H25NO3

Molecular Weight: 375.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccccc1)c1ccccc1OCC(O)CNc1ccccc1

Standard InChI:  InChI=1S/C24H25NO3/c26-21(17-25-20-11-5-2-6-12-20)18-28-24-14-8-7-13-22(24)23(27)16-15-19-9-3-1-4-10-19/h1-14,21,25-26H,15-18H2

Standard InChI Key:  YHTIQUARFRYUQD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.4167   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292    0.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    0.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542    0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -4.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5 10  1  0
  6  2  2  0
  7  2  1  0
  8  9  1  0
  9  4  1  0
 10  8  1  0
 11  7  1  0
 12  5  1  0
 13 11  1  0
 14  8  1  0
 15  1  2  0
 16  3  2  0
 17 12  2  0
 18 12  1  0
 19 13  1  0
 20 13  2  0
 21 15  1  0
 22 21  2  0
 23 20  1  0
 24 17  1  0
 25 18  2  0
 26 19  2  0
 27 23  2  0
 28 25  1  0
 22 16  1  0
 27 26  1  0
 28 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA149234

   1-(2-(2-Hydroxy-3-(phenylamino)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: 375.47

Molecular Weight (Monoisotopic): 375.1834

AlogP: 4.35

#Rotatable Bonds: 10

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.10

CX LogP: 4.30

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.46

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