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

ID: ALA150438

PubChem CID: 44367274

Max Phase: Preclinical

Molecular Formula: C17H20O6

Molecular Weight: 320.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OCc2cc(OC)c(OC)c(OC)c2)cc1O

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

Standard InChI Key:  PJCOYSVLNFEHHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    0.9875    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    0.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792    0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167    1.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -0.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    0.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000    1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167    1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  2  0
  5 10  1  0
  6  3  2  0
  7  2  1  0
  8 11  2  0
  9  6  1  0
 10 12  1  0
 11 18  1  0
 12 14  1  0
 13  1  1  0
 14  9  1  0
 15  3  1  0
 16  2  1  0
 17  4  1  0
 18 10  2  0
 19  8  1  0
 20 13  1  0
 21 15  1  0
 22 16  1  0
 23 19  1  0
  7  9  2  0
  4  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA150438

   2-Methoxy-5-(3,4,5-trimethoxy-benzyloxy)-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: 9.87

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: 0.19

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