4-(2,4-Dichlorobenzylideneamino)naphthalene-1,2-dione

ID: ALA2282728

PubChem CID: 76330850

Max Phase: Preclinical

Molecular Formula: C17H9Cl2NO2

Molecular Weight: 330.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(/N=C\c2ccc(Cl)cc2Cl)c2ccccc2C1=O

Standard InChI:  InChI=1S/C17H9Cl2NO2/c18-11-6-5-10(14(19)7-11)9-20-15-8-16(21)17(22)13-4-2-1-3-12(13)15/h1-9H/b20-9-

Standard InChI Key:  JAZMUFGPUHIKOU-UKWGHVSLSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   15.6573   -1.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6561   -2.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3642   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3624   -1.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0710   -1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0744   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7868   -2.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5003   -2.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4970   -1.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7800   -1.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7755   -0.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2034   -1.2884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7890   -3.7548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4978   -4.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2044   -3.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9096   -4.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6157   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6139   -2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9001   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1969   -2.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9101   -4.9764    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.3200   -2.5198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  2  0
  7 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 16 21  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282728

   4-[(2,4-Dichlorophenyl)methylideneamino]naphthalene-1,2-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: 330.17

Molecular Weight (Monoisotopic): 329.0010

AlogP: 4.22

#Rotatable Bonds: 2

Polar Surface Area: 46.50

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.55

CX LogP: 4.57

CX LogD: 4.57

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.61

Np Likeness Score: -0.51

References

1. Shukla S, Srivastava RS, Shrivastava SK, Sodhi A, Kumar P.  (2013)  Synthesis, characterization, in vitro anticancer activity, and docking of Schiff bases of 4-amino-1,2-naphthoquinone,  22  (4): [10.1007/s00044-012-0150-7]

Source

Source(1):

• Scientific Literature