1-(4-(4-(trifluoromethyl)benzyloxy)-6-hydroxy-7-methoxybenzofuran-5-yl)ethanone

ID: ALA381841

PubChem CID: 11675306

Max Phase: Preclinical

Molecular Formula: C19H15F3O5

Molecular Weight: 380.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(C(C)=O)c(OCc2ccc(C(F)(F)F)cc2)c2ccoc12

Standard InChI:  InChI=1S/C19H15F3O5/c1-10(23)14-15(24)18(25-2)17-13(7-8-26-17)16(14)27-9-11-3-5-12(6-4-11)19(20,21)22/h3-8,24H,9H2,1-2H3

Standard InChI Key:  TXZCADNPYSRWIN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.9596   -1.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6771   -1.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3936   -1.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3877   -0.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9572   -0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6744    0.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5008    0.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6762    1.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3404    0.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1000    0.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956    0.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8079    1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5267    0.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2385    1.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2299    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5130    2.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8041    2.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1109   -1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1165   -2.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8225   -1.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6809   -2.3700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2463   -1.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2486   -2.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9416    2.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6500    3.0167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.3595    1.8882    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.5262    3.3124    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 15 24  1  0
  1  2  2  0
 24 25  1  0
 11 12  1  0
 24 26  1  0
  5  1  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA381841

   1-(4-(4-(Trifluoromethyl)benzyloxy)-6-hydroxy-7-methoxybenzofuran-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: 380.32

Molecular Weight (Monoisotopic): 380.0872

AlogP: 4.95

#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: 4.32

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: 0.37

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