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

ID: ALA382657

PubChem CID: 11595683

Max Phase: Preclinical

Molecular Formula: C22H18O5

Molecular Weight: 362.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C(C)=O)c(O)c(OCc2ccc3ccccc3c2)c2occc12

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

Standard InChI Key:  DQOZWNUMCZSXBX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   12.7029   -7.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7274   -7.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0193   -6.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2953   -7.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9761   -8.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2714   -7.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6386   -8.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9521   -9.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7787   -9.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0404   -5.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7652   -5.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3368   -5.3876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4531   -6.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4047   -8.3370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5925   -6.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3802   -9.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0821   -9.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0535  -10.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7544  -10.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020   -9.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5038   -9.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4789  -10.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1830  -10.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9126  -10.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9336   -9.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2287   -9.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6149   -5.7804    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
 16 17  1  0
  7  8  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
 19 22  2  0
  9  5  1  0
 21 20  2  0
 20 17  1  0
  4  6  1  0
  3 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
  1  2  2  0
 24 25  1  0
 10 12  2  0
 25 26  2  0
 26 21  1  0
  5  1  1  0
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA382657

   1-(6-Hydroxy-4-methoxy-7-(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: 8.56

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.41

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: 0.78

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