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

ID: ALA202692

PubChem CID: 11717498

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(OCc2cccc3ccccc23)c2ccoc12

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

Standard InChI Key:  RMJVHDRIYREEHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.4266  -23.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420  -23.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607  -23.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590  -22.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285  -22.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1478  -22.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784  -21.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543  -21.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145  -21.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5758  -23.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772  -24.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896  -23.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416  -24.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112  -23.7002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734  -22.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093  -24.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879  -22.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024  -22.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289  -21.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7094  -20.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984  -21.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4286  -22.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139  -22.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7114  -23.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4229  -23.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1383  -23.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1373  -22.4634    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
 18 23  2  0
  8  9  1  0
 22 19  2  0
  9  5  1  0
 19 20  1  0
  4  6  1  0
 20 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:

   

   ALA202692

   1-(6-Hydroxy-7-methoxy-4-(naphthalen-1-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: 0.54

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