1-(4,6,8-trichloro-9-hydroxy-1,3,7-trimethoxy-2-dibenzofuranyl)butanone

ID: ALA2409645

PubChem CID: 71727894

Max Phase: Preclinical

Molecular Formula: C19H17Cl3O6

Molecular Weight: 447.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)c1c(OC)c(Cl)c2oc3c(Cl)c(OC)c(Cl)c(O)c3c2c1OC

Standard InChI:  InChI=1S/C19H17Cl3O6/c1-5-6-7(23)8-15(25-2)10-9-14(24)11(20)19(27-4)13(22)17(9)28-18(10)12(21)16(8)26-3/h24H,5-6H2,1-4H3

Standard InChI Key:  AOJFYMTVKJGXCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   16.8636  -10.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5732  -10.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5704   -9.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8618   -8.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8594   -8.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8634  -11.3402    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.2816  -10.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2766   -8.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9858   -9.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2735   -8.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6920   -8.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4012   -9.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1555  -10.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1522   -9.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3800  -10.3694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8973   -9.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3744   -9.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0425   -8.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2325   -8.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7554   -8.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0884   -9.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5218   -7.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6109  -10.2954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.8989   -7.4796    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9425   -8.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6087   -8.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9887  -10.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5658   -7.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 14  1  0
  4  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 13 14  2  0
 14 17  1  0
 16 15  1  0
 15 13  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 18 22  1  0
 21 23  1  0
 19 24  1  0
 20 25  1  0
 25 26  1  0
  7 27  1  0
  5 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409645

   1-(4,6,8-Trichloro-9-hydroxy-1,3,7-trimethoxydibenzofuran-2-yl)butan-1-one

Molecule Features

Natural Product: Yes

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: 447.70

Molecular Weight (Monoisotopic): 446.0091

AlogP: 6.26

#Rotatable Bonds: 6

Polar Surface Area: 78.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.67

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: 1.07

References

1. Kikuchi H, Kubohara Y, Nguyen VH, Katou Y, Oshima Y..  (2013)  Novel chlorinated dibenzofurans isolated from the cellular slime mold, Polysphondylium filamentosum, and their biological activities.,  21  (15): [PMID:23746784] [10.1016/j.bmc.2013.05.022]

Source

Source(1):

• Scientific Literature