2-Chloro-3-(diphenylamino)naphthalene-1,4-dione

ID: ALA551076

PubChem CID: 44139036

Max Phase: Preclinical

Molecular Formula: C22H14ClNO2

Molecular Weight: 359.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(Cl)=C(N(c2ccccc2)c2ccccc2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C22H14ClNO2/c23-19-20(22(26)18-14-8-7-13-17(18)21(19)25)24(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H

Standard InChI Key:  FDLBGLHYVRBXLY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    3.5890  -11.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745  -11.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745  -12.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890  -12.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034  -12.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034  -11.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179  -12.8425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7324  -12.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468  -12.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468  -11.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7324  -11.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1613  -11.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1613  -12.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8758  -12.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5903  -12.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5903  -11.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8758  -11.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468  -13.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468  -10.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179  -11.1925    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0179  -13.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7324  -14.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7324  -14.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179  -15.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034  -14.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034  -14.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  8  9  1  0
  9 18  2  0
 10 19  2  0
  4  5  1  0
 11 20  1  0
  2  3  1  0
  8 11  2  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
  5  6  2  0
  6  1  1  0
 21 22  2  0
 12 13  2  0
 22 23  1  0
  1  2  2  0
 23 24  2  0
 13 14  1  0
 24 25  1  0
  5  7  1  0
 25 26  2  0
 26 21  1  0
  7 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA551076

   2-chloro-3-(N-phenylanilino)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: 359.81

Molecular Weight (Monoisotopic): 359.0713

AlogP: 5.35

#Rotatable Bonds: 3

Polar Surface Area: 37.38

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.99

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.35

References

1. Tandon VK, Maurya HK, Mishra NN, Shukla PK..  (2009)  Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents.,  44  (8): [PMID:19349095] [10.1016/j.ejmech.2009.03.006]

Source

Source(1):

• Scientific Literature