(4-(6-Chloropyridin-3-yl)piperazin-1-yl)(morpholino)methanone

ID: ALA3103333

PubChem CID: 76313801

Max Phase: Preclinical

Molecular Formula: C14H19ClN4O2

Molecular Weight: 310.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCOCC1)N1CCN(c2ccc(Cl)nc2)CC1

Standard InChI:  InChI=1S/C14H19ClN4O2/c15-13-2-1-12(11-16-13)17-3-5-18(6-4-17)14(20)19-7-9-21-10-8-19/h1-2,11H,3-10H2

Standard InChI Key:  LZILQUNTXWVUIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   20.4820   -8.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4809   -9.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1957   -9.8403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9121   -9.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9093   -8.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1939   -8.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6222   -8.1812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3355   -8.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0464   -8.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0475   -7.3563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3316   -6.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6146   -7.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7619   -6.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4764   -7.3563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7619   -6.1188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4731   -8.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1834   -8.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9003   -8.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9023   -7.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1874   -6.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7661   -9.8393    0.0000 Cl  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
M  END

Alternative Forms

1. Parent:

   

   ALA3103333

   [4-(6-Chloropyridin-3-yl)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: 310.79

Molecular Weight (Monoisotopic): 310.1197

AlogP: 1.31

#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: 1.32

CX LogP: 0.66

CX LogD: 0.66

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: -1.87

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