(E)-3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,3,4-trimethoxy-phenyl)-propenone

ID: ALA195840

PubChem CID: 10150010

Max Phase: Preclinical

Molecular Formula: C19H20O6

Molecular Weight: 344.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)c2ccc(OC)c(OC)c2OC)cc1O

Standard InChI:  InChI=1S/C19H20O6/c1-22-16-9-6-12(11-15(16)21)5-8-14(20)13-7-10-17(23-2)19(25-4)18(13)24-3/h5-11,21H,1-4H3/b8-5+

Standard InChI Key:  YCHQRKYXGAHYHC-VMPITWQZSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.6181   -8.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -9.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -9.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1880   -9.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -8.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062   -7.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381   -8.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811   -6.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9510   -7.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -8.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -8.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822   -9.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0961   -8.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903   -8.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3745   -7.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359   -7.7689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503   -8.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321   -9.4192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3328  -10.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -9.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -8.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -7.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -6.9448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6269   -6.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  7  8  1  0
 17 18  1  0
  1 17  1  0
  7  9  2  0
  4  5  1  0
 19 20  1  0
  2 19  1  0
  8 10  2  0
  2  3  1  0
 21 22  1  0
 14 21  1  0
 10 11  1  0
 15 23  1  0
  5  6  2  0
 11 12  2  0
 24 25  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA195840

   (E)-3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,3,4-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: 344.36

Molecular Weight (Monoisotopic): 344.1260

AlogP: 3.32

#Rotatable Bonds: 7

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.83

CX Basic pKa: ┄

CX LogP: 2.96

CX LogD: 2.95

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 0.53

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