1-{6-hydroxy-7-methoxy-4-[(2-methylbenzyl)oxy]-1-benzofuran-5-yl}ethanone

ID: ALA204803

PubChem CID: 11587895

Max Phase: Preclinical

Molecular Formula: C19H18O5

Molecular Weight: 326.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(C(C)=O)c(OCc2ccccc2C)c2ccoc12

Standard InChI:  InChI=1S/C19H18O5/c1-11-6-4-5-7-13(11)10-24-17-14-8-9-23-18(14)19(22-3)16(21)15(17)12(2)20/h4-9,21H,10H2,1-3H3

Standard InChI Key:  VLURLJJGXZUKRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.2179   -1.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9354   -2.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6519   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6460   -1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2155   -1.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9327   -0.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7592    0.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9346    0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5987   -0.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3583   -0.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3540    0.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0662    0.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7851    0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4969    0.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4882    1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7713    1.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0625    1.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3692   -2.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3749   -3.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0808   -1.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9392   -3.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5046   -2.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5070   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7880   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 11 12  1  0
  5  1  1  0
 12 13  2  0
  2  3  1  0
 13 14  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  2  0
  3 18  1  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 18 20  2  0
  4  6  1  0
  2 21  1  0
  4 10  1  0
  1 22  1  0
  5  6  2  0
 22 23  1  0
 10 11  1  0
 13 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA204803

   1-{6-Hydroxy-7-methoxy-4-[(2-methylbenzyl)oxy]-1-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: 326.35

Molecular Weight (Monoisotopic): 326.1154

AlogP: 4.24

#Rotatable Bonds: 5

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.58

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.71

Np Likeness Score: 0.60

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