(4-(4-Chlorobenzoyl)piperazin-1-yl)(morpholino)methanone

ID: ALA3103336

PubChem CID: 34680232

Max Phase: Preclinical

Molecular Formula: C16H20ClN3O3

Molecular Weight: 337.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(Cl)cc1)N1CCN(C(=O)N2CCOCC2)CC1

Standard InChI:  InChI=1S/C16H20ClN3O3/c17-14-3-1-13(2-4-14)15(21)18-5-7-19(8-6-18)16(22)20-9-11-23-12-10-20/h1-4H,5-12H2

Standard InChI Key:  DNTQFSARMMKYRS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.4998  -14.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2059  -13.8199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9125  -14.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6166  -13.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6177  -13.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9086  -12.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1984  -13.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3254  -12.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0331  -13.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3254  -11.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0298  -13.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7334  -14.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4435  -13.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4455  -13.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7374  -12.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7905  -13.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7916  -13.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0832  -12.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3761  -13.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3818  -13.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0908  -14.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6663  -12.6106    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.5028  -15.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
  9 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
  1 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103336

   (4-Chlorophenyl)-[4-(morpholine-4-carbonyl)piperazin-1-yl]methanone

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: 337.81

Molecular Weight (Monoisotopic): 337.1193

AlogP: 1.55

#Rotatable Bonds: 1

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.84

CX LogD: 0.84

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -1.50

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