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

ID: ALA3103335

PubChem CID: 76321041

Max Phase: Preclinical

Molecular Formula: C16H22ClN3O2

Molecular Weight: 323.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCOCC1)N1CCN(Cc2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C16H22ClN3O2/c17-15-3-1-14(2-4-15)13-18-5-7-19(8-6-18)16(21)20-9-11-22-12-10-20/h1-4H,5-13H2

Standard InChI Key:  KCONUSOZXPPQQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.2312  -14.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374  -13.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6440  -14.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3480  -13.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3492  -13.0523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6401  -12.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298  -13.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0569  -12.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7646  -13.0523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0569  -11.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7612  -13.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4649  -14.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1750  -13.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1770  -13.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688  -12.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220  -13.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5231  -13.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147  -12.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075  -13.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133  -13.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222  -14.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978  -12.6601    0.0000 Cl  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
M  END

Alternative Forms

1. Parent:

   

   ALA3103335

   [4-[(4-Chlorophenyl)methyl]piperazin-1-yl]-morpholin-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: 323.82

Molecular Weight (Monoisotopic): 323.1401

AlogP: 1.91

#Rotatable Bonds: 2

Polar Surface Area: 36.02

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.96

CX LogP: 1.49

CX LogD: 1.47

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -1.66

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