4,6-dibromo-5-(3-isopropyl-4-methoxyphenoxy)benzofuran-2-carboxylic acid

ID: ALA245508

PubChem CID: 22228616

Max Phase: Preclinical

Molecular Formula: C19H16Br2O5

Molecular Weight: 484.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Oc2c(Br)cc3oc(C(=O)O)cc3c2Br)cc1C(C)C

Standard InChI:  InChI=1S/C19H16Br2O5/c1-9(2)11-6-10(4-5-14(11)24-3)25-18-13(20)8-15-12(17(18)21)7-16(26-15)19(22)23/h4-9H,1-3H3,(H,22,23)

Standard InChI Key:  SDAAEVHXLRPRFF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.6231    2.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219    2.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3367    1.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0531    2.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0502    2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3349    3.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7630    3.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4790    2.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4788    2.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1939    1.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1862    3.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    1.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9086    3.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9084    4.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942    2.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6888    3.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9020    2.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9074    2.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6985    1.8168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1794    2.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0042    2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4232    1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4102    3.2183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931    2.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7649    1.6477    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.1789    4.1268    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  6  1  1  0
  1 13  1  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 13 15  1  0
 17 18  1  0
  3  4  2  0
  7  8  1  0
  8  9  2  0
  4  5  1  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
  9 10  1  0
 20 21  1  0
 10 18  2  0
 21 22  1  0
  2  3  1  0
 21 23  2  0
 17 11  2  0
 12 24  1  0
 11  8  1  0
  9 25  1  0
  5  6  2  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA245508

   4,6-Dibromo-5-(4-methoxy-3-propan-2-ylphenoxy)-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: 484.14

Molecular Weight (Monoisotopic): 481.9364

AlogP: 6.58

#Rotatable Bonds: 5

Polar Surface Area: 68.90

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: 5.84

CX LogD: 2.37

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.10

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