Morpholino(4-(2-(trifluoromethyl)phenyl)piperazin-1-yl)methanone

ID: ALA3103359

PubChem CID: 76328254

Max Phase: Preclinical

Molecular Formula: C16H20F3N3O2

Molecular Weight: 343.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCOCC1)N1CCN(c2ccccc2C(F)(F)F)CC1

Standard InChI:  InChI=1S/C16H20F3N3O2/c17-16(18,19)13-3-1-2-4-14(13)20-5-7-21(8-6-20)15(23)22-9-11-24-12-10-22/h1-4H,5-12H2

Standard InChI Key:  MERRHWANGSILHO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.4307   -8.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296   -9.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1376   -9.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -9.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445   -8.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358   -7.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506   -7.9097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -8.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613   -7.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -7.0926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2533   -6.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5431   -7.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6701   -6.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3778   -7.0926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6701   -5.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3745   -7.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0781   -8.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7882   -7.9119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7902   -7.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0821   -6.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556   -9.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569  -10.3683    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2627   -9.1414    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2593   -9.9590    0.0000 F   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
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  4 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103359

   Morpholin-4-yl-[4-[2-(trifluoromethyl)phenyl]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: 343.35

Molecular Weight (Monoisotopic): 343.1508

AlogP: 2.28

#Rotatable Bonds: 1

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: ┄

CX LogP: 1.93

CX LogD: 1.93

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -1.56

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