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

ID: ALA364034

PubChem CID: 10215785

Max Phase: Preclinical

Molecular Formula: C20H22O7

Molecular Weight: 374.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/C(=C\c1ccc(OC)c(O)c1)C(=O)c1cc(OC)c(OC)c(OC)c1

Standard InChI:  InChI=1S/C20H22O7/c1-23-15-7-6-12(8-14(15)21)9-16(24-2)19(22)13-10-17(25-3)20(27-5)18(11-13)26-4/h6-11,21H,1-5H3/b16-9-

Standard InChI Key:  FNILUMSXQRNRNV-SXGWCWSVSA-N

Molfile:  

     RDKit          2D

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   -2.2836   -0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5672    0.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700    0.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    1.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8571    1.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    0.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602    2.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5780   -0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795   -1.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -1.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0086   -1.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028   -0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7120    2.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.3601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4274    0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838   -1.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984   -1.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142    0.0806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -1.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293   -2.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    1.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687    2.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
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  3  4  2  0
 15 16  2  0
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  1 17  1  0
 17 18  1  0
  7  9  2  0
  2 19  1  0
  4  5  1  0
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  8 10  2  0
  3 21  1  0
  2  3  1  0
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 10 11  1  0
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  5  6  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA364034

   (Z)-3-(3-Hydroxy-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: 374.39

Molecular Weight (Monoisotopic): 374.1366

AlogP: 3.30

#Rotatable Bonds: 8

Polar Surface Area: 83.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.76

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: 0.61

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