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

ID: ALA191407

PubChem CID: 10155655

Max Phase: Preclinical

Molecular Formula: C19H18F2O5

Molecular Weight: 364.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)/C=C/c2cc(F)c(OC)c(F)c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H18F2O5/c1-23-16-9-12(10-17(24-2)19(16)26-4)15(22)6-5-11-7-13(20)18(25-3)14(21)8-11/h5-10H,1-4H3/b6-5+

Standard InChI Key:  HTYJDJGCSJAUHZ-AATRIKPKSA-N

Molfile:  

     RDKit          2D

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   -1.9130   -9.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -8.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6312   -8.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -8.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869   -8.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2061   -7.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -8.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420   -8.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420   -9.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -9.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6495   -8.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -9.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3430   -8.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -8.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708   -9.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -8.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0578   -7.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -9.7265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -9.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302  -10.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3451  -10.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0809   -8.0412    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -9.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905  -10.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618  -10.5358    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15 12  2  0
 12  9  1  0
 13 14  2  0
 13  1  1  0
  5  6  1  0
 15 16  1  0
  2  3  1  0
  5  7  2  0
 14 17  1  0
  6  8  2  0
 17 18  1  0
  3  4  2  0
 13 19  1  0
  8  9  1  0
 19 20  1  0
  4 14  1  0
  1 21  1  0
  9 10  2  0
 21 22  1  0
  1  2  2  0
 15 23  1  0
 10 11  1  0
 16 24  1  0
 11 16  2  0
 24 25  1  0
  3  5  1  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191407

   (E)-3-(3,5-Difluoro-4-methoxy-phenyl)-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: 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: -0.13

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