4-(3,4-Dimethoxybenzylideneamino)naphthalene-1,2-dione

ID: ALA2282736

PubChem CID: 76309054

Max Phase: Preclinical

Molecular Formula: C19H15NO4

Molecular Weight: 321.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=N\C2=CC(=O)C(=O)c3ccccc32)cc1OC

Standard InChI:  InChI=1S/C19H15NO4/c1-23-17-8-7-12(9-18(17)24-2)11-20-15-10-16(21)19(22)14-6-4-3-5-13(14)15/h3-11H,1-2H3/b20-11-

Standard InChI Key:  MCDIQABCIHQPPX-JAIQZWGSSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   17.3206  -13.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3194  -13.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0275  -14.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0257  -12.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7343  -13.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7377  -13.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4501  -14.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1636  -13.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1602  -13.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4433  -12.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4388  -11.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8667  -12.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4523  -15.2037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1611  -15.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8677  -15.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5729  -15.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2790  -15.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2772  -14.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5634  -13.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8602  -14.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5583  -13.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2634  -12.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9832  -13.9688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6926  -14.3745    0.0000 C   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
 19 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282736

   4-[(3,4-Dimethoxyphenyl)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: 321.33

Molecular Weight (Monoisotopic): 321.1001

AlogP: 2.93

#Rotatable Bonds: 4

Polar Surface Area: 64.96

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.65

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: 0.00

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