3-[4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenyl]-propionic acid

ID: ALA183170

PubChem CID: 10298167

Max Phase: Preclinical

Molecular Formula: C22H19F6NO3

Molecular Weight: 459.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1c[nH]c2ccc(Oc3c(C(F)(F)F)cc(CCC(=O)O)cc3C(F)(F)F)cc12

Standard InChI:  InChI=1S/C22H19F6NO3/c1-11(2)15-10-29-18-5-4-13(9-14(15)18)32-20-16(21(23,24)25)7-12(3-6-19(30)31)8-17(20)22(26,27)28/h4-5,7-11,29H,3,6H2,1-2H3,(H,30,31)

Standard InChI Key:  NMTUNXAZFPBDHE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.2417    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -0.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958    0.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2250    2.3083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.4833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042    1.4708    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -1.7167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -1.4167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -1.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  7  1  0
  5  2  1  0
  6  1  1  0
  7 14  1  0
  8  4  2  0
  9 10  1  0
 10 26  1  0
 11  3  1  0
 12  1  1  0
 13 17  1  0
 14 16  2  0
 15 27  1  0
 16 11  1  0
 17 12  2  0
 18 15  2  0
 19  6  1  0
 20  5  1  0
 21  5  1  0
 22  5  1  0
 23  6  1  0
 24  6  1  0
 25  4  1  0
 26 28  2  0
 27 29  1  0
 28 16  1  0
 29 17  1  0
 30 15  1  0
 31 25  1  0
 32 25  1  0
 13  2  2  0
 10  7  2  0
  8  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA183170

   3-[4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenyl]-propionic 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: 459.39

Molecular Weight (Monoisotopic): 459.1269

AlogP: 7.14

#Rotatable Bonds: 6

Polar Surface Area: 62.32

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.14

CX Basic pKa: ┄

CX LogP: 6.66

CX LogD: 3.20

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -0.15

References

1. Haning H, Woltering M, Mueller U, Schmidt G, Schmeck C, Voehringer V, Kretschmer A, Pernerstorfer J..  (2005)  Novel heterocyclic thyromimetics.,  15  (7): [PMID:15780617] [10.1016/j.bmcl.2005.02.028]

Source

Source(1):

• Scientific Literature