2-(6-(4-hydroxy-3-isopropylphenoxy)-5,7-dimethylbenzofuran-3-yl)acetic acid

ID: ALA248515

PubChem CID: 22228621

Max Phase: Preclinical

Molecular Formula: C21H22O5

Molecular Weight: 354.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(CC(=O)O)coc2c(C)c1Oc1ccc(O)c(C(C)C)c1

Standard InChI:  InChI=1S/C21H22O5/c1-11(2)16-9-15(5-6-18(16)22)26-20-12(3)7-17-14(8-19(23)24)10-25-21(17)13(20)4/h5-7,9-11,22H,8H2,1-4H3,(H,23,24)

Standard InChI Key:  XGIXEBKNKXHCMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -4.2598   -7.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609   -8.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -8.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8297   -8.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8325   -7.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479   -7.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196   -7.2645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4036   -7.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038   -8.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -8.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -7.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9757   -8.9226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057   -7.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -7.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0249   -8.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8178   -8.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977   -8.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -9.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523   -9.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618  -10.1764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678   -8.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177   -8.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9743   -7.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9745   -6.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6887   -7.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -6.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
 14 15  2  0
  6  1  1  0
  1  2  2  0
  5  7  1  0
  3  4  2  0
  7  8  1  0
 13 14  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 16 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  2  0
 19 21  1  0
 10 15  1  0
  9 22  1  0
  2  3  1  0
  1 23  1  0
 14 11  1  0
 23 24  1  0
 11  8  2  0
 23 25  1  0
  5  6  2  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA248515

   2-[6-(4-Hydroxy-3-propan-2-ylphenoxy)-5,7-dimethyl-1-benzofuran-3-yl]acetic 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: 354.40

Molecular Weight (Monoisotopic): 354.1467

AlogP: 5.30

#Rotatable Bonds: 5

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: 4.29

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 2.27

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: 0.29

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