4,6-dibromo-5-(3-(4-fluorobenzoyl)-4-hydroxyphenoxy)benzofuran-2-carboxylic acid

ID: ALA247912

PubChem CID: 22228633

Max Phase: Preclinical

Molecular Formula: C22H11Br2FO6

Molecular Weight: 550.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(Br)c(Oc3ccc(O)c(C(=O)c4ccc(F)cc4)c3)c(Br)cc2o1

Standard InChI:  InChI=1S/C22H11Br2FO6/c23-15-9-17-14(8-18(31-17)22(28)29)19(24)21(15)30-12-5-6-16(26)13(7-12)20(27)10-1-3-11(25)4-2-10/h1-9,26H,(H,28,29)

Standard InChI Key:  GIYRXPZCGDUAFM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    7.4652   -8.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4641   -9.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1789  -10.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8953   -9.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8925   -8.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1771   -8.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6054   -8.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3214   -8.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3212   -9.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0363  -10.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0287   -8.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493  -10.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7507   -8.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7505   -7.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5314   -8.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7445   -8.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7499   -9.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5411   -9.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0219   -9.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8469   -9.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2659   -9.8979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2529   -8.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6073  -10.0397    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.0363   -8.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4673   -7.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -6.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523   -5.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0356   -6.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0390   -7.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7510   -5.1024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0213   -7.5604    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  5  7  1  0
  3  4  2  0
  7  8  1  0
  8  9  2  0
 15 16  1  0
 17 18  1  0
 18 19  1  0
 19 15  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
 10 17  2  0
 20 22  2  0
  2  3  1  0
  9 23  1  0
 16 11  2  0
 13 24  2  0
 11  8  1  0
 14 25  2  0
  5  6  2  0
 25 26  1  0
  2 12  1  0
 26 27  2  0
  6  1  1  0
 27 28  1  0
  1 13  1  0
 28 29  2  0
 29 14  1  0
  1  2  2  0
 27 30  1  0
 13 14  1  0
 11 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA247912

   4,6-Dibromo-5-[3-(4-fluorobenzoyl)-4-hydroxyphenoxy]-1-benzofuran-2-carboxylic acid

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: 550.13

Molecular Weight (Monoisotopic): 547.8906

AlogP: 6.52

#Rotatable Bonds: 5

Polar Surface Area: 96.97

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: 6.70

CX LogD: 2.89

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.32

References

1. Haning H, Mueller U, Schmidt G, Schmeck C, Voehringer V, Kretschmer A, Bischoff H..  (2007)  Novel heterocyclic thyromimetics. Part 2.,  17  (14): [PMID:17499989] [10.1016/j.bmcl.2007.04.085]

Source

Source(1):

• Scientific Literature