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

ID: ALA1914835

PubChem CID: 56647653

Max Phase: Preclinical

Molecular Formula: C29H34ClNO3

Molecular Weight: 443.59

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H33NO3.ClH/c31-26(21-30-19-17-25(18-20-30)24-11-5-2-6-12-24)22-33-29-14-8-7-13-27(29)28(32)16-15-23-9-3-1-4-10-23;/h1-14,25-26,31H,15-22H2;1H

Standard InChI Key:  IHJPRWYCRBWGGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    1.8500   -5.8750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9598   -6.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609   -7.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2461   -7.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5297   -7.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5325   -6.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479   -6.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8196   -6.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1036   -6.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -5.3353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3907   -6.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747   -6.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747   -7.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9595   -7.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2456   -7.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514   -6.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -6.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -7.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133   -8.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981   -9.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968   -9.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3843   -8.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817  -10.2902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842  -11.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732  -11.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9569  -11.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562  -10.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -9.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473  -11.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2504  -12.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623  -12.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1787  -12.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1778  -11.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645  -11.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 12  1  0
  8  9  1  0
  5 18  1  0
 18 19  1  0
  8 10  2  0
 19 20  1  0
  5  6  1  0
 20 21  1  0
  9 11  1  0
 20 22  1  0
  3  4  1  0
 21 23  1  0
 23 24  1  0
 11 12  1  0
  6  7  2  0
 12 13  2  0
  7  2  1  0
 13 14  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  2  3  2  0
 14 15  2  0
 29 30  2  0
  6  8  1  0
 30 31  1  0
 15 16  1  0
 31 32  2  0
  4  5  2  0
 32 33  1  0
 16 17  2  0
 33 34  2  0
 34 29  1  0
 26 29  1  0
M  END

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: 443.59

Molecular Weight (Monoisotopic): 443.2460

AlogP: 5.12

#Rotatable Bonds: 10

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.98

CX LogP: 5.31

CX LogD: 4.63

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: -0.59

References

1. Lowes DJ, Guiguemde WA, Connelly MC, Zhu F, Sigal MS, Clark JA, Lemoff AS, Derisi JL, Wilson EB, Guy RK..  (2011)  Optimization of propafenone analogues as antimalarial leads.,  54  (21): [PMID:21955244] [10.1021/jm2005546]

Source

Source(1):

• Scientific Literature