3-((5-acetyl-6-hydroxy-4-methoxybenzofuran-7-yloxy)methyl)benzoic acid

ID: ALA203646

PubChem CID: 11696117

Max Phase: Preclinical

Molecular Formula: C19H16O7

Molecular Weight: 356.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H16O7/c1-10(20)14-15(21)18(17-13(6-7-25-17)16(14)24-2)26-9-11-4-3-5-12(8-11)19(22)23/h3-8,21H,9H2,1-2H3,(H,22,23)

Standard InChI Key:  JQGKELPNYBZRHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.5585   -6.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5586   -4.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8448   -5.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8471   -4.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0602   -4.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5716   -5.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0566   -5.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2728   -4.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2783   -5.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9966   -6.1353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7085   -4.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9857   -4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9791   -3.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5559   -6.9619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8408   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8382   -8.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223   -8.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1194   -9.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8323   -9.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5498   -9.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5492   -8.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5578   -3.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2719   -3.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2662   -9.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2665  -10.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9805   -9.4291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 11 12  1  0
  4  5  1  0
 24 25  1  0
 24 26  2  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA203646

   3-[(5-Acetyl-6-hydroxy-4-methoxy-1-benzofuran-7-yl)oxymethyl]benzoic acid

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: 356.33

Molecular Weight (Monoisotopic): 356.0896

AlogP: 3.63

#Rotatable Bonds: 6

Polar Surface Area: 106.20

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: -0.07

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: 0.79

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