4-((3-Phenylallylidene)amino)naphthalene-1,2-dione

ID: ALA2282723

PubChem CID: 76309053

Max Phase: Preclinical

Molecular Formula: C19H13NO2

Molecular Weight: 287.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(/N=C\C=C\c2ccccc2)c2ccccc2C1=O

Standard InChI:  InChI=1S/C19H13NO2/c21-18-13-17(15-10-4-5-11-16(15)19(18)22)20-12-6-9-14-7-2-1-3-8-14/h1-13H/b9-6+,20-12-

Standard InChI Key:  WQSPFWHHVYLSNQ-LRFQPHQISA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   23.0574  -19.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0563  -20.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7643  -21.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7625  -19.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4711  -19.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4745  -20.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1869  -21.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9005  -20.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8971  -19.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1801  -19.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1756  -18.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6035  -19.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1891  -22.0302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8979  -22.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6045  -22.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3134  -22.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0199  -22.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7250  -22.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4311  -22.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4293  -21.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7155  -20.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0124  -21.2082    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 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282723

   4-[[(E)-3-phenylprop-2-enylidene]amino]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: 287.32

Molecular Weight (Monoisotopic): 287.0946

AlogP: 3.58

#Rotatable Bonds: 3

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: 5.40

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 0.28

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