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

ID: ALA2282729

PubChem CID: 136264389

Max Phase: Preclinical

Molecular Formula: C17H11NO3

Molecular Weight: 277.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(/N=C\c2ccc(O)cc2)c2ccccc2C1=O

Standard InChI:  InChI=1S/C17H11NO3/c19-12-7-5-11(6-8-12)10-18-15-9-16(20)17(21)14-4-2-1-3-13(14)15/h1-10,19H/b18-10-

Standard InChI Key:  JNJBRPJSZLAGHU-ZDLGFXPLSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   22.5539   -1.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5527   -2.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2608   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2590   -1.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9676   -1.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9710   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6834   -2.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3969   -2.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3936   -1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6766   -1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6721   -0.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1000   -1.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6856   -3.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3944   -4.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1010   -3.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8062   -4.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5123   -3.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5105   -2.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7967   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0935   -2.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2166   -2.5818    0.0000 O   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
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282729

   ---

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: 277.28

Molecular Weight (Monoisotopic): 277.0739

AlogP: 2.62

#Rotatable Bonds: 2

Polar Surface Area: 66.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.78

CX Basic pKa: 4.77

CX LogP: 3.06

CX LogD: 3.04

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: 0.22

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