5-acetyl-7-benzyloxy-6-hydroxy-4-methoxybenzofuran

ID: ALA381920

PubChem CID: 11631003

Max Phase: Preclinical

Molecular Formula: C18H16O5

Molecular Weight: 312.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C(C)=O)c(O)c(OCc2ccccc2)c2occc12

Standard InChI:  InChI=1S/C18H16O5/c1-11(19)14-15(20)18(23-10-12-6-4-3-5-7-12)17-13(8-9-22-17)16(14)21-2/h3-9,20H,10H2,1-2H3

Standard InChI Key:  BDEMWMBDVCGRMW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.9247   -8.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -8.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6383   -7.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -6.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2099   -8.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112   -7.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4232   -6.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9349   -7.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -8.2906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -6.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0672   -7.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3481   -5.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3563   -8.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245   -9.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9211   -5.9705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -9.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387  -10.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2057   -5.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9237  -10.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231  -11.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380  -12.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550  -11.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3520  -10.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  1  2  2  0
 10 12  2  0
  5  1  1  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
 15 18  1  0
  8  9  1  0
 17 19  2  0
  9  5  1  0
 19 20  1  0
  4  6  1  0
 20 21  2  0
  3 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA381920

   5-Acetyl-7-benzyloxy-6-hydroxy-4-methoxybenzofuran

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: 312.32

Molecular Weight (Monoisotopic): 312.0998

AlogP: 3.93

#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: 8.56

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: 0.94

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