(E)-3-(3-Fluoro-4-methoxy-phenyl)-2-methyl-1-(3,4,5-trimethoxy-phenyl)-propenone

ID: ALA426644

PubChem CID: 10155421

Max Phase: Preclinical

Molecular Formula: C20H21FO5

Molecular Weight: 360.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C(\C)C(=O)c2cc(OC)c(OC)c(OC)c2)cc1F

Standard InChI:  InChI=1S/C20H21FO5/c1-12(8-13-6-7-16(23-2)15(21)9-13)19(22)14-10-17(24-3)20(26-5)18(11-14)25-4/h6-11H,1-5H3/b12-8+

Standard InChI Key:  HOTCJDIFBMQISC-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   13.3069   -9.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3057  -10.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0206  -10.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7370  -10.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7341   -9.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0188   -9.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4471   -9.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1631   -9.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4439   -8.1853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1662  -10.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8822  -10.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8837  -11.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5988  -11.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5912  -10.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8760   -9.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0204  -11.4944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3058  -11.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5923   -9.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5921   -8.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5910  -10.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8768  -10.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3070  -10.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3170  -11.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0173  -10.2259    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.0342  -11.8822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0396  -12.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 23  2  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
 22 24  1  0
 11 12  2  0
 23 25  1  0
  6  1  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA426644

   (E)-3-(3-Fluoro-4-methoxy-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: 360.38

Molecular Weight (Monoisotopic): 360.1373

AlogP: 4.15

#Rotatable Bonds: 7

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.22

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