6-(3-(4-hydroxy-3-isopropylphenoxy)-2,4-dimethylbenzyl)-1,3-thiazinane-2,4-dione

ID: ALA392666

PubChem CID: 44441145

Max Phase: Preclinical

Molecular Formula: C22H25NO4S

Molecular Weight: 399.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CC2CC(=O)NC(=O)S2)c(C)c1Oc1ccc(O)c(C(C)C)c1

Standard InChI:  InChI=1S/C22H25NO4S/c1-12(2)18-10-16(7-8-19(18)24)27-21-13(3)5-6-15(14(21)4)9-17-11-20(25)23-22(26)28-17/h5-8,10,12,17,24H,9,11H2,1-4H3,(H,23,25,26)

Standard InChI Key:  TWNAGPAVIUMOMK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -4.5473  -17.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5484  -18.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8336  -19.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172  -18.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200  -17.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8354  -17.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071  -17.4020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911  -17.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913  -18.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762  -19.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838  -17.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2632  -19.0601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2618  -17.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2620  -16.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9762  -17.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052  -19.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638  -17.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2626  -18.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475  -17.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1651  -17.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1664  -18.6091    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798  -19.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937  -18.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895  -17.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8715  -17.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828  -19.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023  -17.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9936  -16.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 13 15  1  0
  3  4  2  0
  9 16  1  0
 17 18  1  0
  7  8  1  0
  8  9  2  0
 17 19  1  0
  4  5  1  0
 20 19  1  0
 20 21  1  0
  9 10  1  0
 10 18  2  0
  2  3  1  0
 17 11  2  0
 11  8  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  5  6  2  0
 22 26  2  0
  2 12  1  0
 24 27  2  0
  6  1  1  0
 11 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA392666

   6-[[3-(4-Hydroxy-3-propan-2-ylphenoxy)-2,4-dimethylphenyl]methyl]-1,3-thiazinane-2,4-dione

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: 399.51

Molecular Weight (Monoisotopic): 399.1504

AlogP: 5.21

#Rotatable Bonds: 5

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.16

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 5.60

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: 0.10

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