1-[6-Hydroxy-4-methoxy-7-(3-methyl-benzyloxy)-benzofuran-5-yl]-ethanone

ID: ALA383465

PubChem CID: 11587894

Max Phase: Preclinical

Molecular Formula: C19H18O5

Molecular Weight: 326.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C(C)=O)c(O)c(OCc2cccc(C)c2)c2occc12

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

Standard InChI Key:  PEBYQEWZDCISKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.3508   -7.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3509   -5.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6370   -6.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6393   -5.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8524   -5.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637   -6.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8488   -7.0412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0651   -5.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0706   -6.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7890   -7.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5009   -5.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7781   -5.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7715   -4.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3482   -8.0249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6330   -8.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6304   -9.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9145   -9.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116  -10.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6245  -10.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3421  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3415   -9.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3501   -4.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0641   -4.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0567  -10.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  4  5  1  0
 12 13  2  0
  5  6  2  0
  6  7  1  0
  1 14  1  0
  7  3  1  0
 14 15  1  0
  8  9  2  0
 15 16  1  0
  3  4  1  0
 16 17  2  0
  3  1  2  0
 17 18  1  0
  1  9  1  0
 18 19  2  0
 19 20  1  0
  8  2  1  0
 20 21  2  0
 21 16  1  0
  2  4  2  0
  2 22  1  0
  8 12  1  0
 22 23  1  0
  9 10  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA383465

   1-[6-Hydroxy-4-methoxy-7-(3-methyl-benzyloxy)-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: 8.56

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.71

Np Likeness Score: 0.68

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