1-(4,6,8-trichloro-1,9-dihydroxy-3,7-dimethoxydibenzo[b,d]furan-2-yl)hexan-1-one

ID: ALA2409646

PubChem CID: 9868940

Max Phase: Preclinical

Molecular Formula: C20H19Cl3O6

Molecular Weight: 461.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(=O)c1c(OC)c(Cl)c2oc3c(Cl)c(OC)c(Cl)c(O)c3c2c1O

Standard InChI:  InChI=1S/C20H19Cl3O6/c1-4-5-6-7-8(24)9-15(25)10-11-16(26)12(21)20(28-3)14(23)19(11)29-18(10)13(22)17(9)27-2/h25-26H,4-7H2,1-3H3

Standard InChI Key:  HANVBLRSGDIVGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   15.9061   -4.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6157   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6129   -3.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9043   -3.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9018   -2.5297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9059   -5.8014    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.3241   -4.9823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3191   -3.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0283   -3.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3160   -2.5237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7345   -3.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4437   -3.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1499   -3.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8591   -3.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1980   -4.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1947   -3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4225   -4.8307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9398   -4.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4169   -3.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0850   -2.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2750   -2.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7979   -3.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1308   -4.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5642   -2.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6534   -4.7567    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9414   -1.9409    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.9850   -3.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6511   -2.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0311   -4.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 16  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
 12 13  1  0
 13 14  1  0
 15 16  2  0
 16 19  1  0
 18 17  1  0
 17 15  1  0
 18 19  2  0
 18 23  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 20 24  1  0
 23 25  1  0
 21 26  1  0
 22 27  1  0
 27 28  1  0
  7 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409646

   1-(4,6,8-Trichloro-1,9-dihydroxy-3,7-dimethoxydibenzofuran-2-yl)hexan-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: 461.73

Molecular Weight (Monoisotopic): 460.0247

AlogP: 6.74

#Rotatable Bonds: 7

Polar Surface Area: 89.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.67

CX Basic pKa: ┄

CX LogP: 6.28

CX LogD: 5.48

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: 1.11

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]

2. Surineni G, Yogeeswari P, Sriram D, Kantevari S..  (2016)  Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides.,  26  (15): [PMID:27317646] [10.1016/j.bmcl.2016.05.085]

Source

Source(1):

• Scientific Literature