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

ID: ALA194925

PubChem CID: 10157446

Max Phase: Preclinical

Molecular Formula: C20H20F2O6

Molecular Weight: 394.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/C(=C\c1cc(F)c(OC)c(F)c1)C(=O)c1cc(OC)c(OC)c(OC)c1

Standard InChI:  InChI=1S/C20H20F2O6/c1-24-15(8-11-6-13(21)19(27-4)14(22)7-11)18(23)12-9-16(25-2)20(28-5)17(10-12)26-3/h6-10H,1-5H3/b15-8-

Standard InChI Key:  NLLPNEJVBYJALY-NVNXTCNLSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.1361  -16.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349  -17.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8497  -17.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5662  -17.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5633  -16.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8479  -15.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2762  -15.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9922  -16.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2731  -15.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9954  -17.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7114  -17.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7128  -18.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4280  -18.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1419  -18.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1361  -17.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4204  -17.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4215  -15.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4213  -15.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201  -17.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060  -17.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8495  -18.3694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349  -18.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8585  -18.7586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8627  -19.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7052  -15.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7020  -15.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8476  -17.1028    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4307  -19.5900    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
  1 17  1  0
 17 18  1  0
  7  9  2  0
  2 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
  3 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 14 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
  8 25  1  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 15 27  1  0
  1  2  2  0
 13 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA194925

   (Z)-3-(3,5-Difluoro-4-methoxy-phenyl)-2-methoxy-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: 394.37

Molecular Weight (Monoisotopic): 394.1228

AlogP: 3.87

#Rotatable Bonds: 8

Polar Surface Area: 63.22

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: 0.06

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