1-(6-hydroxy-7-methoxy-4-(naphthalen-2-ylmethoxy)benzofuran-5-yl)ethanone

ID: ALA204255

PubChem CID: 11703260

Max Phase: Preclinical

Molecular Formula: C22H18O5

Molecular Weight: 362.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(C(C)=O)c(OCc2ccc3ccccc3c2)c2ccoc12

Standard InChI:  InChI=1S/C22H18O5/c1-13(23)18-19(24)22(25-2)21-17(9-10-26-21)20(18)27-12-14-7-8-15-5-3-4-6-16(15)11-14/h3-11,24H,12H2,1-2H3

Standard InChI Key:  JIELYSIFLYPDGU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   10.9799  -23.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6915  -24.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4139  -23.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4197  -23.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9893  -23.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7123  -22.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5502  -21.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7269  -21.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3804  -22.4825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1253  -24.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1193  -25.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8428  -23.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6836  -25.1170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2608  -24.2747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1378  -22.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5511  -23.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8486  -23.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5667  -22.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2752  -23.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9929  -22.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5702  -21.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2849  -21.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9972  -21.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7147  -21.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7211  -20.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0040  -20.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2894  -20.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 13  1  0
  2  3  1  0
  1 14  1  0
  4 15  1  0
  3  4  2  0
 14 16  1  0
  6  7  1  0
 15 17  1  0
  7  8  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
 20 23  2  0
  4  6  1  0
 22 21  2  0
 21 18  1  0
  3 10  1  0
  5  6  2  0
 22 23  1  0
 10 11  1  0
 23 24  1  0
  1  2  2  0
 24 25  2  0
 10 12  2  0
 25 26  1  0
  5  1  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA204255

   1-(6-Hydroxy-7-methoxy-4-(naphthalen-2-ylmethoxy)benzofuran-5-yl)ethanone

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: 362.38

Molecular Weight (Monoisotopic): 362.1154

AlogP: 5.08

#Rotatable Bonds: 5

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: 8.58

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.41

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: 0.68

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