N-[4-(1-Cyclobutylpiperidin-4-yloxy)phenyl]-2-(1,1-dioxo-1-thiomorpholin-4-yl)acetamide dihydrochloride

ID: ALA4520938

PubChem CID: 155542570

Max Phase: Preclinical

Molecular Formula: C21H33Cl2N3O4S

Molecular Weight: 421.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.Cl.O=C(CN1CCS(=O)(=O)CC1)Nc1ccc(OC2CCN(C3CCC3)CC2)cc1

Standard InChI:  InChI=1S/C21H31N3O4S.2ClH/c25-21(16-23-12-14-29(26,27)15-13-23)22-17-4-6-19(7-5-17)28-20-8-10-24(11-9-20)18-2-1-3-18;;/h4-7,18,20H,1-3,8-16H2,(H,22,25);2*1H

Standard InChI Key:  UOLGHEFPYJBKJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    8.5152  -11.1964    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.5457   -7.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1374   -8.4082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.9622   -8.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235   -8.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223   -9.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1372   -9.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8536   -9.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8507   -8.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1354   -7.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7090   -7.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946   -8.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2758   -7.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636   -8.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5596   -9.2276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739   -9.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -9.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5687   -9.6465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2825   -9.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9976   -9.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2813   -8.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7115   -9.2306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444   -9.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319  -10.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280  -10.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4232   -9.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1348   -9.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4229   -7.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7049   -8.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8598  -11.0786    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 23  1  0
 15 23  1  0
 22 27  1  0
 22 30  1  0
 27 28  1  0
 28  3  1  0
  3 29  1  0
 29 30  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: 421.56

Molecular Weight (Monoisotopic): 421.2035

AlogP: 1.75

#Rotatable Bonds: 6

Polar Surface Area: 78.95

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 9.11

CX LogP: 0.54

CX LogD: -1.17

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: -1.53

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