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

ID: ALA245504

PubChem CID: 44441125

Max Phase: Preclinical

Molecular Formula: C18H16O5

Molecular Weight: 312.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cc(Oc2ccc3oc(C(=O)O)cc3c2)ccc1O

Standard InChI:  InChI=1S/C18H16O5/c1-10(2)14-9-13(3-5-15(14)19)22-12-4-6-16-11(7-12)8-17(23-16)18(20)21/h3-10,19H,1-2H3,(H,20,21)

Standard InChI Key:  UVMZHKLHOZBKQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.6425    2.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437    2.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9290    1.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2155    2.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    3.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    3.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867    2.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870    2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0720    1.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    3.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3585    1.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3571    3.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3573    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0712    2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    3.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    2.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415    2.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4325    1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    2.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7382    2.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    1.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442    3.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 11  2  0
 11  8  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA245504

   5-(4-Hydroxy-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: 312.32

Molecular Weight (Monoisotopic): 312.0998

AlogP: 4.75

#Rotatable Bonds: 4

Polar Surface Area: 79.90

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: 4.15

CX LogD: 0.69

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: 0.08

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