(E)-3-(4-Methoxy-3-nitro-phenyl)-2-methyl-1-(3,4,5-trimethoxy-phenyl)-propenone

ID: ALA364517

PubChem CID: 10157011

Max Phase: Preclinical

Molecular Formula: C20H21NO7

Molecular Weight: 387.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C(\C)C(=O)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C20H21NO7/c1-12(8-13-6-7-16(25-2)15(9-13)21(23)24)19(22)14-10-17(26-3)20(28-5)18(11-14)27-4/h6-11H,1-5H3/b12-8+

Standard InChI Key:  PTXFUOFGDDVWNW-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.6806  -14.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818  -15.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669  -16.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505  -15.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534  -14.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687  -14.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404  -14.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756  -14.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436  -13.5270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1787  -15.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8947  -15.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962  -16.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113  -17.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037  -15.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885  -14.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9671  -16.8360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817  -17.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952  -14.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954  -13.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966  -16.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107  -15.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195  -15.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3295  -16.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0309  -15.5669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227  -14.7419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494  -15.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467  -17.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521  -18.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 22 14  2  0
 14 11  1  0
  5  7  1  0
  8 15  1  0
  3  4  2  0
  3 16  1  0
  7  8  1  0
 16 17  1  0
  1 18  1  0
  7  9  2  0
 18 19  1  0
  4  5  1  0
  2 20  1  0
  8 10  2  0
 20 21  1  0
 22 23  1  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 24 25  2  0
 24 26  1  0
 22 24  1  0
 12 13  1  0
 23 27  1  0
 13 23  2  0
 27 28  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA364517

   (E)-3-(4-Methoxy-3-nitro-phenyl)-2-methyl-1-(3,4,5-trimethoxy-phenyl)-propenone

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: 387.39

Molecular Weight (Monoisotopic): 387.1318

AlogP: 3.92

#Rotatable Bonds: 8

Polar Surface Area: 97.13

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: -0.27

References

1. Ducki S, Mackenzie G, Lawrence NJ, Snyder JP..  (2005)  Quantitative structure-activity relationship (5D-QSAR) study of combretastatin-like analogues as inhibitors of tubulin assembly.,  48  (2): [PMID:15658859] [10.1021/jm049444m]

2. Ducki S, Rennison D, Woo M, Kendall A, Chabert JF, McGown AT, Lawrence NJ..  (2009)  Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: synthesis and biological evaluation of antivascular activity.,  17  (22): [PMID:19837593] [10.1016/j.bmc.2009.09.039]

Source

Source(1):

• Scientific Literature