4-(4-Hydroxy-3-methoxybenzylideneamino)naphthalene-1,2-dione

ID: ALA2282738

PubChem CID: 136240202

Max Phase: Preclinical

Molecular Formula: C18H13NO4

Molecular Weight: 307.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=N\C2=CC(=O)C(=O)c3ccccc32)ccc1O

Standard InChI:  InChI=1S/C18H13NO4/c1-23-17-8-11(6-7-15(17)20)10-19-14-9-16(21)18(22)13-5-3-2-4-12(13)14/h2-10,20H,1H3/b19-10-

Standard InChI Key:  BMRHVGQKPLCKQW-GRSHGNNSSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    1.0799  -18.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0788  -19.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868  -19.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850  -17.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936  -18.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970  -19.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094  -19.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230  -19.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196  -18.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2026  -17.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1981  -17.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6260  -17.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116  -20.4371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9205  -20.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270  -20.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322  -20.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0383  -20.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0366  -19.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228  -19.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196  -19.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3177  -18.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0228  -17.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7426  -19.2021    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
 19 21  1  0
 21 22  1  0
 18 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282738

   ---

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: 307.31

Molecular Weight (Monoisotopic): 307.0845

AlogP: 2.63

#Rotatable Bonds: 3

Polar Surface Area: 75.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.25

CX Basic pKa: 4.59

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: 0.34

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