2-methyl-3-(2-(4-(2-nitrobenzoyl)piperazin-1-yl)ethoxy)-4H-pyran-4-one

ID: ALA4744743

PubChem CID: 162648794

Max Phase: Preclinical

Molecular Formula: C19H21N3O6

Molecular Weight: 387.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1occc(=O)c1OCCN1CCN(C(=O)c2ccccc2[N+](=O)[O-])CC1

Standard InChI:  InChI=1S/C19H21N3O6/c1-14-18(17(23)6-12-27-14)28-13-11-20-7-9-21(10-8-20)19(24)15-4-2-3-5-16(15)22(25)26/h2-6,12H,7-11,13H2,1H3

Standard InChI Key:  YKAFNIIEBPXDGP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   15.2336   -7.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9413   -6.8595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5261   -6.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8205   -7.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8162   -8.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5238   -8.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2356   -8.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5280   -6.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9429   -8.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6490   -7.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3567   -6.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0644   -7.2680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7721   -6.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0644   -8.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4798   -7.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4798   -8.0852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1876   -8.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7721   -8.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1876   -9.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8953   -8.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6030   -8.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3102   -8.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3106   -7.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5979   -6.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8936   -7.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6046   -9.3175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3117   -9.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8963   -9.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  7  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  3  8  2  0
  7  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 13 15  1  0
 14 18  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 17 19  2  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
 21 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4744743

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 387.39

Molecular Weight (Monoisotopic): 387.1430

AlogP: 1.69

#Rotatable Bonds: 6

Polar Surface Area: 106.13

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.38

CX LogP: 1.55

CX LogD: 1.54

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -1.32

References

1. Xiang S,Huang D,He Q,Li J,Tam KY,Zhang SL,He Y.  (2020)  Development of dual inhibitors targeting pyruvate dehydrogenase kinases and human lactate dehydrogenase A: High-throughput virtual screening, synthesis and biological validation.,  203  [PMID:32688200] [10.1016/j.ejmech.2020.112579]

Source

Source(1):

• Scientific Literature