rac-1,1,1-trifluoro-2-(4-((2-(piperidin-1-yl)-4-(trifluoromethyl)thiazol-5-yl)sulfonyl)phenyl)propan-2-ol

ID: ALA4276816

PubChem CID: 145982480

Max Phase: Preclinical

Molecular Formula: C18H20F6N2O3S2

Molecular Weight: 490.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(O)(c1ccc(S(=O)(=O)C2SC(N3CCCCC3)=NC2C(F)(F)F)cc1)C(F)(F)F

Standard InChI:  InChI=1S/C18H20F6N2O3S2/c1-16(27,18(22,23)24)11-5-7-12(8-6-11)31(28,29)14-13(17(19,20)21)25-15(30-14)26-9-3-2-4-10-26/h5-8,13-14,27H,2-4,9-10H2,1H3

Standard InChI Key:  AADZRZOWFKIFTL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    6.1740   -5.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -6.2023    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0030   -5.4831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3059   -6.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3048   -7.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0196   -7.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7360   -7.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332   -6.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0178   -6.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0735   -6.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2533   -6.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -7.5743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6021   -8.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2922   -7.6407    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8021   -6.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746   -5.3771    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783   -6.1586    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3103   -5.4432    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6317   -8.9158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4512   -7.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4525   -8.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1650   -7.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1615   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8801   -7.8508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1637   -6.6144    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.8740   -7.0190    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -9.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567  -10.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838  -10.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3849  -10.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3589   -9.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4  2  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 13 19  1  0
  7 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 22 24  1  0
 22 25  1  0
 22 26  1  0
 19 27  1  0
 19 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4276816

   ---

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: 490.49

Molecular Weight (Monoisotopic): 490.0820

AlogP: 4.08

#Rotatable Bonds: 3

Polar Surface Area: 69.97

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.23

CX Basic pKa: 3.55

CX LogP: 4.28

CX LogD: -0.03

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: -0.81

References

1. Chakka N, Andrews KL, Berry LM, Bregman H, Gunaydin H, Huang L, Guzman-Perez A, Plant MH, Simard JR, Gingras J, DiMauro EF..  (2017)  Applications of parallel synthetic lead hopping and pharmacophore-based virtual screening in the discovery of efficient glycine receptor potentiators.,  137  [PMID:28575722] [10.1016/j.ejmech.2017.05.036]

2. Chakka N, Andrews KL, Berry LM, Bregman H, Gunaydin H, Huang L, Guzman-Perez A, Plant MH, Simard JR, Gingras J, DiMauro EF..  (2017)  Applications of parallel synthetic lead hopping and pharmacophore-based virtual screening in the discovery of efficient glycine receptor potentiators.,  137  [PMID:28575722] [10.1016/j.ejmech.2017.05.036]

3. Chakka N, Andrews KL, Berry LM, Bregman H, Gunaydin H, Huang L, Guzman-Perez A, Plant MH, Simard JR, Gingras J, DiMauro EF..  (2017)  Applications of parallel synthetic lead hopping and pharmacophore-based virtual screening in the discovery of efficient glycine receptor potentiators.,  137  [PMID:28575722] [10.1016/j.ejmech.2017.05.036]

Source

Source(1):

• Scientific Literature