2-Chloro-3-(4-(4-nitrophenyl)piperazin-1-yl)naphthalene-1,4-dione

ID: ALA2424736

PubChem CID: 2943566

Max Phase: Preclinical

Molecular Formula: C20H16ClN3O4

Molecular Weight: 397.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(Cl)=C(N2CCN(c3ccc([N+](=O)[O-])cc3)CC2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C20H16ClN3O4/c21-17-18(20(26)16-4-2-1-3-15(16)19(17)25)23-11-9-22(10-12-23)13-5-7-14(8-6-13)24(27)28/h1-8H,9-12H2

Standard InChI Key:  HKTMRQQAVNTTRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    9.7519  -12.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0375  -12.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0375  -11.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7519  -11.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4664  -11.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1809  -11.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8953  -11.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8953  -12.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1809  -12.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4664  -12.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7519  -13.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7519  -10.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3230  -11.2418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6085  -11.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8940  -11.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8940  -10.4168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6085  -10.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3230  -10.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1796  -10.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4651  -10.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506  -10.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506   -9.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4651   -8.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1796   -9.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0362   -8.7668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0362   -7.9418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -9.1793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3230  -12.8918    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  1 11  2  0
  4 12  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 25 26  2  0
 25 27  1  0
 22 25  1  0
 16 19  1  0
  3 13  1  0
  2 28  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2424736

   2-Chloro-3-[4-(4-nitrophenyl)piperazin-1-yl]naphthalene-1,4-dione

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: 397.82

Molecular Weight (Monoisotopic): 397.0829

AlogP: 3.25

#Rotatable Bonds: 3

Polar Surface Area: 83.76

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.29

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -0.94

References

1. Ibis C, Tuyun AF, Bahar H, Ayla SS, Stasevych MV, Musyanovych RY, Komarovska-Porokhnyavets O, Novikov V.  (2013)  Nucleophilic substitution reactions of 1,4-naphthoquinone and biologic properties of novel S-, S,S-, N-, and N,S-substituted 1,4-naphthoquinone derivatives,  [10.1007/s00044-013-0806-y]

Source

Source(1):

• Scientific Literature