1-(4-(4-tert-butylbenzyloxy)-6-hydroxy-7-methoxybenzofuran-5-yl)ethanone

ID: ALA381476

PubChem CID: 11696332

Max Phase: Preclinical

Molecular Formula: C22H24O5

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H24O5/c1-13(23)17-18(24)21(25-5)20-16(10-11-26-20)19(17)27-12-14-6-8-15(9-7-14)22(2,3)4/h6-11,24H,12H2,1-5H3

Standard InChI Key:  ORHSBRGJHWPZKG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.9346   -7.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521   -8.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686   -7.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627   -6.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9322   -6.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6494   -6.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758   -5.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6512   -5.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -6.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -6.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706   -5.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829   -5.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017   -5.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2135   -5.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2049   -4.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4880   -3.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7791   -4.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -8.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915   -8.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7975   -7.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -8.9283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2213   -8.1063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -8.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9166   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6250   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3345   -4.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5012   -3.2460    0.0000 C   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:

   

   ALA381476

   1-(4-(4-Tert-butylbenzyloxy)-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: 368.43

Molecular Weight (Monoisotopic): 368.1624

AlogP: 5.23

#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: 8.58

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.96

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: 0.48

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