3-(4-ethoxy-6-hydroxy-7-methoxybenzofuran-5-yl)-1-(3-hydroxyphenyl)-3-oxopropene

ID: ALA204437

PubChem CID: 11646072

Max Phase: Preclinical

Molecular Formula: C20H18O6

Molecular Weight: 354.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1c(C(=O)/C=C/c2cccc(O)c2)c(O)c(OC)c2occc12

Standard InChI:  InChI=1S/C20H18O6/c1-3-25-18-14-9-10-26-19(14)20(24-2)17(23)16(18)15(22)8-7-12-5-4-6-13(21)11-12/h4-11,21,23H,3H2,1-2H3/b8-7+

Standard InChI Key:  CQSCZYNTADGZOI-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.0810   -8.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0812   -6.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3670   -7.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3692   -7.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5819   -6.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0930   -7.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5783   -8.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7959   -7.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8014   -7.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5201   -8.2484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5092   -6.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5026   -5.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0784   -9.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3630   -9.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0804   -5.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7943   -5.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7934   -4.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2273   -6.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9374   -6.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6555   -6.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6619   -7.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3792   -8.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0904   -7.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0797   -6.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3619   -6.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7884   -6.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
  1 13  1  0
  4  5  1  0
 13 14  1  0
  5  6  2  0
  2 15  1  0
  6  7  1  0
 15 16  1  0
  7  3  1  0
 16 17  1  0
  8  9  2  0
 11 18  1  0
  3  4  1  0
 18 19  2  0
  3  1  2  0
 19 20  1  0
  1  9  1  0
 20 21  2  0
 21 22  1  0
  8 11  1  0
 22 23  2  0
  9 10  1  0
 23 24  1  0
  8  2  1  0
 24 25  2  0
 25 20  1  0
 11 12  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA204437

   3-(4-Ethoxy-6-hydroxy-7-methoxybenzofuran-5-yl)-1-(3-hydroxyphenyl)-3-oxopropene

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: 354.36

Molecular Weight (Monoisotopic): 354.1103

AlogP: 4.15

#Rotatable Bonds: 6

Polar Surface Area: 89.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.61

CX Basic pKa: ┄

CX LogP: 4.13

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: 0.98

References

1. Harvey AJ, Baell JB, Toovey N, Homerick D, Wulff H..  (2006)  A new class of blockers of the voltage-gated potassium channel Kv1.3 via modification of the 4- or 7-position of khellinone.,  49  (4): [PMID:16480279] [10.1021/jm050839v]

Source

Source(1):

• Scientific Literature