4,6-dibromo-5-(3-((4-fluorophenyl)(hydroxy)methyl)-4-hydroxyphenoxy)benzofuran-2-carboxylic acid

ID: ALA247913

PubChem CID: 21018711

Max Phase: Preclinical

Molecular Formula: C22H13Br2FO6

Molecular Weight: 552.15

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/C22H13Br2FO6/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/h1-9,20,26-27H,(H,28,29)

Standard InChI Key:  PTLUYEZLNAZYDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.6931  -13.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6943  -14.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794  -14.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630  -14.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2659  -13.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9812  -13.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529  -13.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369  -13.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372  -14.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1220  -14.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296  -13.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4091  -14.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077  -13.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079  -12.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731  -13.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861  -13.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915  -14.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827  -14.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636  -13.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6886  -13.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1076  -14.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0946  -13.1857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510  -14.7563    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.1220  -13.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911  -11.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6909  -11.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4060  -10.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1227  -11.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1194  -11.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073   -9.8191    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1370  -12.2770    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  1  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:

   

   ALA247913

   4,6-Dibromo-5-{3-[(4-fluorophenyl)(hydroxy)methyl]-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: 552.15

Molecular Weight (Monoisotopic): 549.9063

AlogP: 6.37

#Rotatable Bonds: 5

Polar Surface Area: 100.13

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 2.14

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.12

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