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

ID: ALA2282737

PubChem CID: 76334438

Max Phase: Preclinical

Molecular Formula: C17H10N2O4

Molecular Weight: 306.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(/N=C\c2ccccc2[N+](=O)[O-])c2ccccc2C1=O

Standard InChI:  InChI=1S/C17H10N2O4/c20-16-9-14(12-6-2-3-7-13(12)17(16)21)18-10-11-5-1-4-8-15(11)19(22)23/h1-10H/b18-10-

Standard InChI Key:  LNUURTYYRPBCAY-ZDLGFXPLSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   25.8639  -13.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8628  -14.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5708  -14.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5690  -13.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2777  -13.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2810  -14.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9934  -14.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7070  -14.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7036  -13.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9866  -13.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9822  -12.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4100  -13.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9956  -15.7609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7045  -16.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4111  -15.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1162  -16.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8223  -15.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8206  -14.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1068  -14.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4036  -14.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1153  -16.9856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8233  -17.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4078  -17.3946    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
 21 22  2  0
 21 23  1  0
 16 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2282737

   4-[(2-Nitrophenyl)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: 306.28

Molecular Weight (Monoisotopic): 306.0641

AlogP: 2.82

#Rotatable Bonds: 3

Polar Surface Area: 89.64

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.23

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: -0.52

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