Morpholino(4-(quinolin-3-yl)piperazin-1-yl)methanone

ID: ALA3103344

PubChem CID: 76321042

Max Phase: Preclinical

Molecular Formula: C18H22N4O2

Molecular Weight: 326.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCOCC1)N1CCN(c2cnc3ccccc3c2)CC1

Standard InChI:  InChI=1S/C18H22N4O2/c23-18(22-9-11-24-12-10-22)21-7-5-20(6-8-21)16-13-15-3-1-2-4-17(15)19-14-16/h1-4,13-14H,5-12H2

Standard InChI Key:  QKSWJXIYGJXJSC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   29.0265  -14.4604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7362  -14.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7334  -13.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0247  -12.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4395  -12.8170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1461  -13.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8502  -12.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8513  -11.9999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1422  -11.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4320  -12.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5590  -11.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2667  -11.9999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5590  -10.7741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2634  -12.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9670  -13.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6771  -12.8192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6791  -12.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9710  -11.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3185  -14.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3208  -13.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6148  -12.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9061  -13.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9078  -14.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6143  -14.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 20  1  0
  3  5  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 12 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103344

   Morpholin-4-yl-(4-quinolin-3-ylpiperazin-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: 326.40

Molecular Weight (Monoisotopic): 326.1743

AlogP: 1.81

#Rotatable Bonds: 1

Polar Surface Area: 48.91

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.66

CX LogP: 1.21

CX LogD: 1.21

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -1.64

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