4,6-dibromo-5-(4-hydroxy-3-isopropylphenoxy)benzofuran-2-carboxylic acid

Names and Identifiers

Canonical SMILES: CC(C)c1cc(Oc2c(Br)cc3oc(C(=O)O)cc3c2Br)ccc1O

Standard InChI: InChI=1S/C18H14Br2O5/c1-8(2)10-5-9(3-4-13(10)21)24-17-12(19)7-14-11(16(17)20)6-15(25-14)18(22)23/h3-8,21H,1-2H3,(H,22,23)

Standard InChI Key: VYQVOAZEEZYHRP-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -3.5639   -0.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8503   -1.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521   -0.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -0.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -1.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072   -1.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -0.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785   -0.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2787    0.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929   -0.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022   -0.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7153   -0.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7207   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119   -1.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9928   -0.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8177   -0.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367   -1.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -0.1482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4219   -1.7188    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078    0.7605    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  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
  9 24  1  0
 11  8  1  0
 11 25  1  0
M  END

Alternative Forms

Parent:

ALA395954
4,6-Dibromo-5-(4-hydroxy-3-propan-2-ylphenoxy)-1-benzofuran-2-carboxylic acid

Associated Targets(Human)

THRA Tclin Thyroid hormone receptor (146 Activities)

Discover Target: THRA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 470.11	Molecular Weight (Monoisotopic): 467.9208	AlogP: 6.28	#Rotatable Bonds: 4
Polar Surface Area: 79.90	Molecular Species: ACID	HBA: 4	HBD: 2
#RO5 Violations: 1	HBA (Lipinski): 5	HBD (Lipinski): 2	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.10	CX Basic pKa: ┄	CX LogP: 5.69	CX LogD: 2.23
Aromatic Rings: 3	Heavy Atoms: 25	QED Weighted: 0.47	Np Likeness Score: 0.17

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