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

ID: ALA3103345

PubChem CID: 76331930

Max Phase: Preclinical

Molecular Formula: C17H21N3O2

Molecular Weight: 299.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1ccc(N2CCN(C(=O)N3CCOCC3)CC2)cc1

Standard InChI:  InChI=1S/C17H21N3O2/c1-2-15-3-5-16(6-4-15)18-7-9-19(10-8-18)17(21)20-11-13-22-14-12-20/h1,3-6H,7-14H2

Standard InChI Key:  OFWSHLLNOKGGBN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.8269  -17.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8258  -18.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338  -19.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435  -18.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407  -17.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321  -17.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9468  -17.4189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6534  -17.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3575  -17.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586  -16.6017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495  -16.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9393  -16.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0663  -16.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7740  -16.6017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0663  -15.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7707  -17.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4743  -17.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1844  -17.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1864  -16.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4783  -16.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181  -19.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4100  -19.4714    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
 21 22  3  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103345

   [4-(4-Ethynylphenyl)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: 299.37

Molecular Weight (Monoisotopic): 299.1634

AlogP: 1.24

#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: 3.31

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -1.65

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