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

ID: ALA150463

PubChem CID: 10380369

Max Phase: Preclinical

Molecular Formula: C16H19NO5

Molecular Weight: 305.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Nc2cc(OC)c(OC)c(OC)c2)cc1O

Standard InChI:  InChI=1S/C16H19NO5/c1-19-13-6-5-10(7-12(13)18)17-11-8-14(20-2)16(22-4)15(9-11)21-3/h5-9,17-18H,1-4H3

Standard InChI Key:  MJYKDEBIQGCYQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    1.8042   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -2.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -3.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -1.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -4.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -3.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -5.0250    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 10  1  0
  9  4  1  0
 10  9  1  0
 11 12  2  0
 12 14  1  0
 13  1  1  0
 14 10  2  0
 15  3  1  0
 16  2  1  0
 17  7  1  0
 18 11  1  0
 19 13  1  0
 20 16  1  0
 21 15  1  0
 22 18  1  0
  4  6  2  0
 11  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA150463

   2-Methoxy-5-(3,4,5-trimethoxy-phenylamino)-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: 305.33

Molecular Weight (Monoisotopic): 305.1263

AlogP: 3.17

#Rotatable Bonds: 6

Polar Surface Area: 69.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.09

CX Basic pKa: 1.74

CX LogP: 2.48

CX LogD: 2.48

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: -0.15

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