5-[(E)-3-Hydroxy-2-methyl-3-(3,4,5-trimethoxy-phenyl)-propenyl]-2-methoxy-phenol

ID: ALA191957

PubChem CID: 10309096

Max Phase: Preclinical

Molecular Formula: C20H24O6

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C(\C)C(O)c2cc(OC)c(OC)c(OC)c2)cc1O

Standard InChI:  InChI=1S/C20H24O6/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/h6-11,19,21-22H,1-5H3/b12-8+

Standard InChI Key:  VTPCPBBVWDRRAV-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.6194  -18.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6182  -19.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3331  -20.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0495  -19.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0466  -18.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313  -18.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7596  -18.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4756  -18.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7564  -17.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4787  -19.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1885  -18.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9045  -18.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9045  -19.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6197  -20.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3336  -19.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3278  -18.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6120  -18.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9048  -18.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046  -17.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9034  -20.0434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893  -19.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3329  -20.8694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6183  -21.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0392  -18.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0501  -20.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0543  -20.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  7  9  1  0
 18 19  1  0
  4  5  1  0
  2 20  1  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
  3 22  1  0
  8 11  2  0
 22 23  1  0
  5  6  2  0
 16 24  1  0
 11 12  1  0
 15 25  1  0
  6  1  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191957

   5-[(E)-3-Hydroxy-2-methyl-3-(3,4,5-trimethoxy-phenyl)-propenyl]-2-methoxy-phenol

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: 360.41

Molecular Weight (Monoisotopic): 360.1573

AlogP: 3.56

#Rotatable Bonds: 7

Polar Surface Area: 77.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.84

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: 0.66

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