5-acetyl-4,7-benzyloxy-6-hydroxybenzofuran

ID: ALA203909

PubChem CID: 11538313

Max Phase: Preclinical

Molecular Formula: C24H20O5

Molecular Weight: 388.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1c(O)c(OCc2ccccc2)c2occc2c1OCc1ccccc1

Standard InChI:  InChI=1S/C24H20O5/c1-16(25)20-21(26)24(29-15-18-10-6-3-7-11-18)23-19(12-13-27-23)22(20)28-14-17-8-4-2-5-9-17/h2-13,26H,14-15H2,1H3

Standard InChI Key:  LLIUIMCUXHPION-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    4.9229   -9.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -7.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -9.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -8.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4232   -7.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -8.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -9.2693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380   -8.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6435   -9.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203  -10.2540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2046  -10.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9223   -6.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583   -9.4296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3515   -7.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3450   -6.9382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0700   -8.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020  -11.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2074   -6.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2066   -5.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227   -5.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222   -4.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068   -4.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -4.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944   -5.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845  -11.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815  -12.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1952  -13.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9134  -12.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128  -11.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 14  1  0
  5  6  2  0
 14 15  2  0
  6  7  1  0
 14 16  1  0
  7  3  1  0
 11 17  1  0
  8  9  2  0
 12 18  1  0
  3  4  1  0
 18 19  1  0
  3  1  2  0
 19 20  2  0
  1  9  1  0
 20 21  1  0
  1 10  1  0
 21 22  2  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
 24 19  1  0
  8  2  1  0
 17 25  2  0
  2 12  1  0
 25 26  1  0
  2  4  2  0
 26 27  2  0
  9 13  1  0
 27 28  1  0
  4  5  1  0
 28 29  2  0
 29 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA203909

   5-Acetyl-4,7-benzyloxy-6-hydroxybenzofuran

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: 388.42

Molecular Weight (Monoisotopic): 388.1311

AlogP: 5.50

#Rotatable Bonds: 7

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.56

CX Basic pKa: ┄

CX LogP: 5.17

CX LogD: 5.14

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: 0.64

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