4-((1H-indol-3-yl)methyleneamino)naphthalene-1,2-dione

ID: ALA2282722

PubChem CID: 136244988

Max Phase: Preclinical

Molecular Formula: C19H12N2O2

Molecular Weight: 300.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(/N=C\c2c[nH]c3ccccc23)c2ccccc2C1=O

Standard InChI:  InChI=1S/C19H12N2O2/c22-18-9-17(14-6-1-2-7-15(14)19(18)23)21-11-12-10-20-16-8-4-3-5-13(12)16/h1-11,20H/b21-11-

Standard InChI Key:  SVXPVSWHWZLING-NHDPSOOVSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   15.2611  -18.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2599  -19.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9680  -19.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9662  -18.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6748  -18.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6782  -19.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3906  -19.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1041  -19.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1007  -18.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3838  -18.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3793  -17.4784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8072  -18.2967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3928  -20.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1016  -21.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8082  -20.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6913  -19.7705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8925  -19.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1019  -20.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5576  -21.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8118  -21.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6097  -22.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1531  -21.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8961  -20.6414    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 19  1  0
 18 16  1  0
 16 17  1  0
 17 15  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282722

   ---

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: 300.32

Molecular Weight (Monoisotopic): 300.0899

AlogP: 3.39

#Rotatable Bonds: 2

Polar Surface Area: 62.29

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.65

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: 0.04

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