4-(3,4,5-Trimethoxybenzylideneamino)naphthalene-1,2-dione

ID: ALA2282735

PubChem CID: 71577320

Max Phase: Preclinical

Molecular Formula: C20H17NO5

Molecular Weight: 351.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=N\C2=CC(=O)C(=O)c3ccccc32)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H17NO5/c1-24-17-8-12(9-18(25-2)20(17)26-3)11-21-15-10-16(22)19(23)14-7-5-4-6-13(14)15/h4-11H,1-3H3/b21-11-

Standard InChI Key:  SGJGHYUJOMAUPE-NHDPSOOVSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.3137  -12.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3126  -13.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0206  -13.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0188  -12.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7275  -12.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7309  -13.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4432  -13.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1568  -13.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1534  -12.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4365  -12.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4320  -11.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598  -12.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4455  -14.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1543  -15.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8609  -14.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5660  -15.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2722  -14.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2704  -13.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5566  -13.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8534  -13.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5515  -12.6943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2566  -12.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9764  -13.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6858  -13.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9808  -15.1431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9826  -15.9603    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 15  1  0
 19 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 17 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2282735

   4-(3,4,5-Trimethoxybenzylideneamino)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: 351.36

Molecular Weight (Monoisotopic): 351.1107

AlogP: 2.94

#Rotatable Bonds: 5

Polar Surface Area: 74.19

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.49

CX LogP: 2.89

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: 0.12

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