Morpholino(4-(4-nitrophenyl)piperazin-1-yl)methanone

ID: ALA3103356

PubChem CID: 3136316

Max Phase: Preclinical

Molecular Formula: C15H20N4O4

Molecular Weight: 320.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCOCC1)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1

Standard InChI:  InChI=1S/C15H20N4O4/c20-15(18-9-11-23-12-10-18)17-7-5-16(6-8-17)13-1-3-14(4-2-13)19(21)22/h1-4H,5-12H2

Standard InChI Key:  QBXDVYMXHRSGQQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.2520   -3.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -4.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589   -5.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686   -4.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658   -3.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -3.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3719   -3.3863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0785   -3.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7826   -3.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -2.5691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0746   -2.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -2.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914   -2.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -2.5692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914   -1.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1958   -3.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8994   -3.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6096   -3.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6115   -2.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9034   -2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409   -5.0279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5403   -5.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336   -4.6188    0.0000 O   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  2  0
 21 23  1  0
  2 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3103356

   Morpholin-4-yl[4-(4-nitrophenyl)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: 320.35

Molecular Weight (Monoisotopic): 320.1485

AlogP: 1.17

#Rotatable Bonds: 2

Polar Surface Area: 79.16

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.28

CX LogP: 0.99

CX LogD: 0.99

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.77

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