N-(3-(5,6-Diethyl-4(3H)-pyrimidone-2-yl)-4-n-propoxyphenyl)-2-(piperidin-1-yl)acetamide

ID: ALA4572238

PubChem CID: 136197398

Max Phase: Preclinical

Molecular Formula: C24H34N4O3

Molecular Weight: 426.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(NC(=O)CN2CCCCC2)cc1-c1nc(CC)c(CC)c(=O)[nH]1

Standard InChI:  InChI=1S/C24H34N4O3/c1-4-14-31-21-11-10-17(25-22(29)16-28-12-8-7-9-13-28)15-19(21)23-26-20(6-3)18(5-2)24(30)27-23/h10-11,15H,4-9,12-14,16H2,1-3H3,(H,25,29)(H,26,27,30)

Standard InChI Key:  MUBCHHXJJJJCOU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   28.1256  -23.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1245  -24.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8325  -25.1045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5422  -24.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5394  -23.8724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8308  -23.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8283  -22.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4178  -23.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4176  -22.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4165  -25.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7091  -24.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2470  -25.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2470  -25.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9545  -26.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6626  -25.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6586  -25.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9505  -24.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9470  -23.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6530  -23.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3624  -23.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0684  -23.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9554  -27.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6635  -27.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6644  -28.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3708  -27.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0790  -27.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7862  -27.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0798  -28.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4944  -27.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7880  -28.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4953  -28.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  6  7  2  0
  1  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  4 12  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 27 29  1  0
 28 30  1  0
 29 31  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4572238

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 426.56

Molecular Weight (Monoisotopic): 426.2631

AlogP: 3.77

#Rotatable Bonds: 9

Polar Surface Area: 87.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.00

CX Basic pKa: 7.11

CX LogP: 3.27

CX LogD: 3.31

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: -1.51

References

1. Wang Z, Jiang X, Zhang X, Tian G, Yang R, Wu J, Zou X, Liu Z, Yang X, Wu C, Shi J, Li J, Suo J, Wang Y, Zhang R, Xu Z, Gong X, He Y, Zhu W, Aisa HA, Jiang H, Xu Y, Shen J..  (2019)  Pharmacokinetics-Driven Optimization of 4(3 H)-Pyrimidinones as Phosphodiesterase Type 5 Inhibitors Leading to TPN171, a Clinical Candidate for the Treatment of Pulmonary Arterial Hypertension.,  62  (10): [PMID:31021628] [10.1021/acs.jmedchem.9b00123]

Source

Source(1):

• Scientific Literature