2-(5-(4-hydroxy-3-isopropylphenoxy)-4,6-dimethyl-2,3-dihydrobenzofuran-2-yl)acetic acid

ID: ALA248315

PubChem CID: 22228623

Max Phase: Preclinical

Molecular Formula: C21H24O5

Molecular Weight: 356.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(c(C)c1Oc1ccc(O)c(C(C)C)c1)CC(CC(=O)O)O2

Standard InChI:  InChI=1S/C21H24O5/c1-11(2)16-8-14(5-6-18(16)22)26-21-12(3)7-19-17(13(21)4)9-15(25-19)10-20(23)24/h5-8,11,15,22H,9-10H2,1-4H3,(H,23,24)

Standard InChI Key:  DYCBQLSLNKIBEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -3.0389   -3.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401   -4.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253   -5.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088   -4.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6117   -3.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3271   -3.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -3.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828   -3.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -4.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5322   -5.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -3.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7549   -5.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7535   -3.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7537   -2.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4679   -3.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0272   -3.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403   -3.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -4.8748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5178   -4.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8969   -5.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427   -4.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7617   -4.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5867   -4.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558   -5.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5172   -2.5645    0.0000 C   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  1  0
  9 10  1  0
  9 21  1  0
 10 18  2  0
 20 22  1  0
  2  3  1  0
 22 23  1  0
 17 11  2  0
 23 24  2  0
 11  8  1  0
 23 25  1  0
  5  6  2  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA248315

   2-[5-(4-Hydroxy-3-propan-2-ylphenoxy)-4,6-dimethyl-2,3-dihydro-1-benzofuran-2-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: 356.42

Molecular Weight (Monoisotopic): 356.1624

AlogP: 4.70

#Rotatable Bonds: 5

Polar Surface Area: 75.99

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 1.82

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: 0.69

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