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

ID: ALA95119

PubChem CID: 10027874

Max Phase: Preclinical

Molecular Formula: C29H34N2O4

Molecular Weight: 474.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N2CCN(CC(O)COc3ccccc3C(=O)CCc3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C29H34N2O4/c1-34-26-14-12-24(13-15-26)31-19-17-30(18-20-31)21-25(32)22-35-29-10-6-5-9-27(29)28(33)16-11-23-7-3-2-4-8-23/h2-10,12-15,25,32H,11,16-22H2,1H3

Standard InChI Key:  DKKOAQAPFLBSMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
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    2.8849  -23.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5997  -24.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3162  -23.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3133  -22.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979  -22.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0262  -22.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7422  -22.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231  -21.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4552  -22.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1712  -22.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1712  -23.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863  -24.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002  -23.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5945  -22.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8787  -22.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313  -24.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326  -25.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7477  -25.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490  -26.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4615  -25.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641  -26.6902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4617  -27.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727  -27.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8889  -27.5144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8896  -26.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740  -26.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5986  -27.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954  -28.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3081  -29.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0245  -28.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0237  -27.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3104  -27.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7386  -29.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4534  -28.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 17  1  0
 17 18  1  0
  7  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 19 21  1  0
  2  3  1  0
 20 22  1  0
 22 23  1  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1  2  2  0
 13 14  2  0
 28 29  2  0
  5  7  1  0
 29 30  1  0
 14 15  1  0
 30 31  2  0
  3  4  2  0
 31 32  1  0
 15 16  2  0
 32 33  2  0
 33 28  1  0
 25 28  1  0
 16 11  1  0
 31 34  1  0
  7  8  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA95119

   1-(2-(2-Hydroxy-3-(4-(4-methoxyphenyl)piperazin-1-yl)propoxy)phenyl)-3-phenylpropan-1-one

2. Alternative Forms:

   

   ALA95119

   1-[2-[2-Hydroxy-3-[4-(4-methoxyphenyl)piperazin-1-yl]propoxy]phenyl]-3-phenylpropan-1-one;hydrochloride

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: 474.60

Molecular Weight (Monoisotopic): 474.2519

AlogP: 4.07

#Rotatable Bonds: 11

Polar Surface Area: 62.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.70

CX LogP: 4.62

CX LogD: 4.54

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.42

Np Likeness Score: -0.87

References

1. Chiba P, Burghofer S, Richter E, Tell B, Moser A, Ecker G..  (1995)  Synthesis, pharmacologic activity, and structure-activity relationships of a series of propafenone-related modulators of multidrug resistance.,  38  (14): [PMID:7629817] [10.1021/jm00014a031]

2. Ecker G, Chiba P, Hitzler M, Schmid D, Visser K, Cordes HP, Csöllei J, Seydel JK, Schaper KJ..  (1996)  Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance.,  39  (24): [PMID:8941391] [10.1021/jm960384x]

3. 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]

4. 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