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

ID: ALA203540

PubChem CID: 11667565

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(OCc2ccc(C(=O)O)cc2)c2occc12

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

Standard InChI Key:  GLLMKLUQYCJFDE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.2335    0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2336    2.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5198    1.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5221    1.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7352    2.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2466    1.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7316    0.8635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9478    1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9533    1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6716    0.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3835    1.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6607    2.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6541    3.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2309   -0.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5158   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5132   -1.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7973   -1.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7944   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5073   -3.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2248   -2.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2242   -1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2328    3.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9469    3.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5060   -3.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7907   -4.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2197   -4.2401    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
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA203540

   4-[(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: 4.06

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: -0.05

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: 0.87

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