1-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-3-phenyl-propan-1-one

ID: ALA5289840

Max Phase: Preclinical

Molecular Formula: C19H22N2O2

Molecular Weight: 310.40

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccccc1)N1CCN(c2ccc(O)cc2)CC1

Standard InChI:  InChI=1S/C19H22N2O2/c22-18-9-7-17(8-10-18)20-12-14-21(15-13-20)19(23)11-6-16-4-2-1-3-5-16/h1-5,7-10,22H,6,11-15H2

Standard InChI Key:  AHBHZZLUODBWMS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.5803    0.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -0.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839   -0.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839    0.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544    0.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381    0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316    1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    0.6035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -0.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111   -0.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -0.2010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1343   -0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1343   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -1.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5674   -1.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2839   -1.8104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5674   -0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -0.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178    0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915    1.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316    1.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  7  2  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 14  2  0
 13 21  1  0
 21 22  1  0
 10 22  1  0
  9 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289840

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 310.40

Molecular Weight (Monoisotopic): 310.1681

AlogP: 2.67

#Rotatable Bonds: 4

Polar Surface Area: 43.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.30

CX Basic pKa: 4.35

CX LogP: 3.13

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.94

Np Likeness Score: -0.85

References

1. Sheth G, Shah SR, Sengupta P, Jarag T, Chimanwala S, Sairam KVVM, Jain V, Talwar R, Dhanave A, Raviya M, Menon S, Trivedi S, Chitturi TR..  (2023)  In the Quest for Potent and Selective Malic Enzyme 3 Inhibitors for the Treatment of Pancreatic Ductal Adenocarcinoma.,  14  (1.0): [PMID:36655126] [10.1021/acsmedchemlett.2c00369]

Source

Source(1):

• Scientific Literature