[2-Methoxy-5-(3,4,5-trimethoxy-benzyloxy)-phenyl]-methanol

ID: ALA153243

PubChem CID: 44367324

Max Phase: Preclinical

Molecular Formula: C18H22O6

Molecular Weight: 334.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OCc2cc(OC)c(OC)c(OC)c2)cc1CO

Standard InChI:  InChI=1S/C18H22O6/c1-20-15-6-5-14(9-13(15)10-19)24-11-12-7-16(21-2)18(23-4)17(8-12)22-3/h5-9,19H,10-11H2,1-4H3

Standard InChI Key:  LUCQOHOTQAOSBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    0.6125    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -0.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125    0.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2750    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  8  2  0
  5 10  2  0
  6  3  2  0
  7  2  1  0
  8 11  1  0
  9  6  1  0
 10 17  1  0
 11 12  1  0
 12 14  1  0
 13  1  1  0
 14  9  1  0
 15  3  1  0
 16  2  1  0
 17 11  2  0
 18  5  1  0
 19  4  1  0
 20 19  1  0
 21 13  1  0
 22 16  1  0
 23 15  1  0
 24 18  1  0
  9  7  2  0
  5  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA153243

   [2-Methoxy-5-(3,4,5-trimethoxy-benzyloxy)-phenyl]-methanol

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: 334.37

Molecular Weight (Monoisotopic): 334.1416

AlogP: 2.79

#Rotatable Bonds: 8

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.14

CX LogD: 2.14

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: 0.05

References

1. Lawrence NJ, Rennison D, Woo M, McGown AT, Hadfield JA..  (2001)  Antimitotic and cell growth inhibitory properties of combretastatin A-4-like ethers.,  11  (1): [PMID:11140732] [10.1016/s0960-894x(00)00596-5]

2. 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]

Source

Source(1):

• Scientific Literature