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

ID: ALA356370

PubChem CID: 44367275

Max Phase: Preclinical

Molecular Formula: C16H18O6

Molecular Weight: 306.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Oc2cc(OC)c(OC)c(OC)c2)cc1O

Standard InChI:  InChI=1S/C16H18O6/c1-18-13-6-5-10(7-12(13)17)22-11-8-14(19-2)16(21-4)15(9-11)20-3/h5-9,17H,1-4H3

Standard InChI Key:  OJRSPUQFMNDPAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    3.5125   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -1.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -3.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -3.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -4.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -5.3792    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  1  0
  5  3  2  0
  6  2  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10  4  1  0
 11 12  2  0
 12 14  1  0
 13  1  1  0
 14  9  2  0
 15  3  1  0
 16  2  1  0
 17  7  1  0
 18 11  1  0
 19 13  1  0
 20 15  1  0
 21 16  1  0
 22 18  1  0
  4  6  2  0
  7 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA356370

   2-Methoxy-5-(3,4,5-trimethoxy-phenoxy)-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: 306.31

Molecular Weight (Monoisotopic): 306.1103

AlogP: 3.22

#Rotatable Bonds: 6

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: 9.49

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: 0.32

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]

4. Bedos-Belval F, Rouch A, Vanucci-Bacque C, Baltas M.  (2012)  Diaryl ether derivatives as anticancer agents a review,  3  (11): [10.1039/C2MD20199B]

Source

Source(1):

• Scientific Literature