(4-(4-Chlorophenyl)piperazin-1-yl)(thiomorpholino)methanone

ID: ALA3103341

PubChem CID: 76324692

Max Phase: Preclinical

Molecular Formula: C15H20ClN3OS

Molecular Weight: 325.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCSCC1)N1CCN(c2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C15H20ClN3OS/c16-13-1-3-14(4-2-13)17-5-7-18(8-6-17)15(20)19-9-11-21-12-10-19/h1-4H,5-12H2

Standard InChI Key:  OXCXCDMSPPIXFG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   29.5372  -24.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5360  -25.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2441  -25.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9537  -25.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9509  -24.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2423  -24.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6571  -24.2412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3636  -24.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0677  -24.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0688  -23.4240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3597  -23.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6495  -23.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7765  -23.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4843  -23.4241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7766  -22.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8280  -25.8836    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.4809  -24.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1845  -24.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8947  -24.2434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.8966  -23.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1885  -23.0122    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  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
  2 16  1  0
 14 17  1  0
 14 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103341

   [4-(4-Chlorophenyl)piperazin-1-yl]-thiomorpholin-4-ylmethanone

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: 325.87

Molecular Weight (Monoisotopic): 325.1016

AlogP: 2.63

#Rotatable Bonds: 1

Polar Surface Area: 26.79

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.68

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: -1.79

References

1. Flanagan JU, Atwell GJ, Heinrich DM, Brooke DG, Silva S, Rigoreau LJ, Trivier E, Turnbull AP, Raynham T, Jamieson SM, Denny WA..  (2014)  Morpholylureas are a new class of potent and selective inhibitors of the type 5 17-β-hydroxysteroid dehydrogenase (AKR1C3).,  22  (3): [PMID:24411201] [10.1016/j.bmc.2013.12.050]

2. Endo, Satoshi S and 16 more authors.  2017-10-26  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.  [PMID:28976752]

Source

Source(1):

• Scientific Literature