3-(3-Hydroxy-4-methoxy-phenyl)-2-methyl-1-(3,4,5-trimethoxy-phenyl)-propan-1-one

ID: ALA193257

PubChem CID: 10215598

Max Phase: Preclinical

Molecular Formula: C20H24O6

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC(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/h6-7,9-12,21H,8H2,1-5H3

Standard InChI Key:  LHEHPZIQKYMDSG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.8069  -13.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057  -14.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5206  -15.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370  -14.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2341  -13.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188  -13.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9471  -13.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631  -13.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9439  -12.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6662  -14.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3760  -13.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0920  -13.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0920  -14.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8072  -15.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5211  -14.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5153  -13.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7995  -13.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923  -13.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921  -12.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909  -15.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768  -14.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204  -15.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058  -16.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2267  -13.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2376  -15.0503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2418  -15.8752    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  2  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  1  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:

   

   ALA193257

   3-(3-Hydroxy-4-methoxy-phenyl)-2-methyl-1-(3,4,5-trimethoxy-phenyl)-propan-1-one

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: 3.49

#Rotatable Bonds: 8

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.90

CX Basic pKa: ┄

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: 0.40

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