N-[4-(1-Cyclobutylpiperidin-4-yloxy)phenyl]-2-(1-ethoxycarbonyl piperazin-4-yl)acetamide dihydrochloride

ID: ALA4476066

PubChem CID: 155537748

Max Phase: Preclinical

Molecular Formula: C24H38Cl2N4O4

Molecular Weight: 444.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)N1CCN(CC(=O)Nc2ccc(OC3CCN(C4CCC4)CC3)cc2)CC1.Cl.Cl

Standard InChI:  InChI=1S/C24H36N4O4.2ClH/c1-2-31-24(30)28-16-14-26(15-17-28)18-23(29)25-19-6-8-21(9-7-19)32-22-10-12-27(13-11-22)20-4-3-5-20;;/h6-9,20,22H,2-5,10-18H2,1H3,(H,25,29);2*1H

Standard InChI Key:  SPHXQTQHNWMMOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   36.0643  -24.1018    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.9691  -21.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9679  -22.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6827  -22.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3991  -22.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3963  -21.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6809  -21.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2545  -21.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5402  -21.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8214  -21.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1092  -21.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1051  -22.3774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8196  -22.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5380  -22.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1143  -22.7964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8281  -22.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5432  -22.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8268  -21.5577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2570  -22.3805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3900  -22.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5938  -22.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3775  -23.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1736  -23.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9688  -22.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6804  -22.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6834  -21.5608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9685  -21.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2505  -21.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3988  -21.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1123  -21.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4006  -20.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.8277  -21.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5413  -21.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5857  -24.1607    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 20  1  0
 12 20  1  0
 19 24  1  0
 19 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 32 33  1  0
M  END

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: 444.58

Molecular Weight (Monoisotopic): 444.2737

AlogP: 2.79

#Rotatable Bonds: 7

Polar Surface Area: 74.35

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 9.11

CX LogP: 1.93

CX LogD: 0.22

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.70

Np Likeness Score: -1.45

References

1. Nirogi R, Shinde A, Mohammed AR, Badange RK, Reballi V, Bandyala TR, Saraf SK, Bojja K, Manchineella S, Achanta PK, Kandukuri KK, Subramanian R, Benade V, Palacharla RC, Jayarajan P, Pandey S, Jasti V..  (2019)  Discovery and Development of N-[4-(1-Cyclobutylpiperidin-4-yloxy)phenyl]-2-(morpholin-4-yl)acetamide Dihydrochloride (SUVN-G3031): A Novel, Potent, Selective, and Orally Active Histamine H₃ Receptor Inverse Agonist with Robust Wake-Promoting Activity.,  62  (3): [PMID:30629436] [10.1021/acs.jmedchem.8b01280]

Source

Source(1):

• Scientific Literature