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

ID: ALA1914844

PubChem CID: 56647654

Max Phase: Preclinical

Molecular Formula: C29H35ClN2O3

Molecular Weight: 458.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N2CCN(CC(O)COc3ccccc3C(=O)CCc3ccccc3)CC2)cc1.Cl

Standard InChI:  InChI=1S/C29H34N2O3.ClH/c1-23-11-14-25(15-12-23)31-19-17-30(18-20-31)21-26(32)22-34-29-10-6-5-9-27(29)28(33)16-13-24-7-3-2-4-8-24;/h2-12,14-15,26,32H,13,16-22H2,1H3;1H

Standard InChI Key:  JVZSQIMZZQMQGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   16.3500   -6.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1527   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1516   -7.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8664   -7.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5828   -7.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5800   -6.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -6.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2929   -6.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0089   -6.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2898   -5.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7218   -6.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4378   -6.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4378   -7.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1530   -7.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8669   -7.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8611   -6.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1454   -6.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2980   -7.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2992   -8.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0144   -9.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0157   -9.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7282   -8.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7308  -10.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7283  -11.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4393  -11.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1556  -11.1769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1563  -10.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4407   -9.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8692  -11.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8621  -12.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5748  -12.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2912  -12.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2903  -11.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5770  -11.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0053  -12.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 26 29  1  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
 17 12  1  0
 32 35  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: 458.60

Molecular Weight (Monoisotopic): 458.2569

AlogP: 4.37

#Rotatable Bonds: 10

Polar Surface Area: 53.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.80

CX LogP: 5.29

CX LogD: 5.20

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: -0.97

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