2-Methoxy-5-(3,4,5-trimethoxy-phenoxymethyl)-phenol

ID: ALA345556

PubChem CID: 10336128

Max Phase: Preclinical

Molecular Formula: C17H20O6

Molecular Weight: 320.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(COc2cc(OC)c(OC)c(OC)c2)cc1O

Standard InChI:  InChI=1S/C17H20O6/c1-19-14-6-5-11(7-13(14)18)10-23-12-8-15(20-2)17(22-4)16(9-12)21-3/h5-9,18H,10H2,1-4H3

Standard InChI Key:  JXIPAFNBJWGSFY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -2.4250   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -0.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4625   -1.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958    0.7958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792    0.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3125    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  2  0
  5  2  1  0
  6  9  2  0
  7  4  1  0
  8 11  2  0
  9 12  1  0
 10  7  1  0
 11 18  1  0
 12 17  1  0
 13  1  1  0
 14  2  1  0
 15  3  1  0
 16  6  1  0
 17 10  1  0
 18 12  2  0
 19  8  1  0
 20 13  1  0
 21 15  1  0
 22 14  1  0
 23 19  1  0
  7  5  2  0
  8  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA345556

   2-Methoxy-5-(3,4,5-trimethoxy-phenoxymethyl)-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: 320.34

Molecular Weight (Monoisotopic): 320.1260

AlogP: 3.01

#Rotatable Bonds: 7

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: 9.81

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: 0.21

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]

3. Uddin R, Naz A, Akhtar N, Zaheer ul Haq.  (2013)  Development of robust QSAR model using rapid overlay of crystal structures (ROCS) based alignment: a test case of Tubulin inhibitors,  22  (7): [10.1007/s00044-012-0327-0]

Source

Source(1):

• Scientific Literature