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

ID: ALA192221

PubChem CID: 10215648

Max Phase: Preclinical

Molecular Formula: C19H18F2O5

Molecular Weight: 364.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)/C=C/c2cc(F)c(OC)c(F)c2)c(OC)c1OC

Standard InChI:  InChI=1S/C19H18F2O5/c1-23-16-8-6-12(17(24-2)19(16)26-4)15(22)7-5-11-9-13(20)18(25-3)14(21)10-11/h5-10H,1-4H3/b7-5+

Standard InChI Key:  CETSHXXRKLPUFX-FNORWQNLSA-N

Molfile:  

     RDKit          2D

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   -2.6713    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    1.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896    1.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613    1.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453    1.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9644    2.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323    1.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8912    1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    1.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6124    0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1051    0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1014    1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8208   -0.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5340    0.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -0.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328   -0.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934    2.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808    2.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8159    1.5343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8162    2.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3225    1.5713    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035   -0.9191    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 15  1  1  0
  5  6  1  0
 15 16  2  0
  2  3  1  0
  5  7  2  0
 15 17  1  0
  6  8  2  0
 17 18  1  0
  3  4  2  0
 14 19  1  0
  8  9  1  0
 19 20  1  0
  4 16  1  0
  4 21  1  0
  9 10  2  0
 21 22  1  0
  1  2  2  0
 16 23  1  0
 10 11  1  0
 23 24  1  0
 11 14  2  0
 13 25  1  0
  3  5  1  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA192221

   (E)-3-(3,5-Difluoro-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: 364.34

Molecular Weight (Monoisotopic): 364.1122

AlogP: 3.90

#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: 3.55

CX LogD: 3.55

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.07

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