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

ID: ALA3103363

Cas Number: 586996-95-4

PubChem CID: 754983

Max Phase: Preclinical

Molecular Formula: C16H23N3O3

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N2CCN(C(=O)N3CCOCC3)CC2)cc1

Standard InChI:  InChI=1S/C16H23N3O3/c1-21-15-4-2-14(3-5-15)17-6-8-18(9-7-17)16(20)19-10-12-22-13-11-19/h2-5H,6-13H2,1H3

Standard InChI Key:  LQTPRRLRTAQMEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.7650  -13.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639  -14.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719  -14.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816  -14.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1788  -13.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701  -13.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8849  -13.2132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915  -13.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2956  -13.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967  -12.3961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5876  -11.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8774  -12.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0044  -11.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7121  -12.3961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0044  -11.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7088  -13.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4124  -13.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1225  -13.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245  -12.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4164  -11.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559  -14.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485  -14.4465    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
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  2 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103363

   4-(4-Methoxyphenyl)piperazinyl morpholin-4-yl ketone

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: 305.38

Molecular Weight (Monoisotopic): 305.1739

AlogP: 1.27

#Rotatable Bonds: 2

Polar Surface Area: 45.25

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.98

CX LogP: 0.89

CX LogD: 0.89

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -1.40

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