6-(5-Bromothiophen-2-yl)-4-(4-(2-hydroxyphenyl)piperazin-1-yl)-2-oxo-2H-pyran-3-carbonitrile

ID: ALA4863721

PubChem CID: 164622167

Max Phase: Preclinical

Molecular Formula: C20H16BrN3O3S

Molecular Weight: 458.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(N2CCN(c3ccccc3O)CC2)cc(-c2ccc(Br)s2)oc1=O

Standard InChI:  InChI=1S/C20H16BrN3O3S/c21-19-6-5-18(28-19)17-11-15(13(12-22)20(26)27-17)24-9-7-23(8-10-24)14-3-1-2-4-16(14)25/h1-6,11,25H,7-10H2

Standard InChI Key:  NECOWWJCCRGHSV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.6821  -16.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3941  -15.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3941  -15.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6821  -14.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9701  -15.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9655  -14.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6852  -13.7620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1097  -14.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8254  -14.1829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1079  -16.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4084  -13.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4135  -12.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7025  -12.1133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9846  -12.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9778  -13.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7087  -11.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4280  -10.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4346  -10.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7227   -9.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0028  -10.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9997  -10.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1382  -11.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2574  -16.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5050  -15.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9556  -16.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3712  -17.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1773  -17.0697    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0388  -17.9997    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  6  2  0
  4  7  1  0
  3  8  1  0
  8  9  3  0
  2 10  2  0
  7 11  1  0
  7 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 17 22  1  0
  5 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4863721

   ---

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: 458.34

Molecular Weight (Monoisotopic): 457.0096

AlogP: 4.03

#Rotatable Bonds: 3

Polar Surface Area: 80.71

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.20

CX Basic pKa: 2.35

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.98

References

1. Mishra S, Parmar N, Chandrakar P, Sharma CP, Parveen S, Vats RP, Seth A, Goel A, Kar S..  (2021)  Design, synthesis, in vitro and in vivo biological evaluation of pyranone-piperazine analogs as potent antileishmanial agents.,  221  [PMID:33992928] [10.1016/j.ejmech.2021.113516]

Source

Source(1):

• Scientific Literature