1-(7-(3-nitrobenzyloxy)-6-hydroxy-4-methoxybenzofuran-5-yl)ethanone

ID: ALA203647

PubChem CID: 11667583

Max Phase: Preclinical

Molecular Formula: C18H15NO7

Molecular Weight: 357.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C(C)=O)c(O)c(OCc2cccc([N+](=O)[O-])c2)c2occc12

Standard InChI:  InChI=1S/C18H15NO7/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

Standard InChI Key:  YQJJVDMMQACJSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -3.0792  -13.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791  -12.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7930  -13.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7907  -12.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776  -12.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662  -12.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812  -13.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3649  -12.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3594  -13.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410  -13.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9291  -12.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519  -12.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585  -11.2711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818  -14.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7970  -14.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996  -15.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5155  -16.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184  -17.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055  -17.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879  -17.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885  -16.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799  -11.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658  -10.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699  -17.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555  -17.0511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696  -18.2890    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  2  0
 24 26  1  0
 20 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA203647

   1-(7-(3-Nitrobenzyloxy)-6-hydroxy-4-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: 357.32

Molecular Weight (Monoisotopic): 357.0849

AlogP: 3.84

#Rotatable Bonds: 6

Polar Surface Area: 112.04

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.56

CX Basic pKa: ┄

CX LogP: 3.39

CX LogD: 3.36

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: 0.29

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