US8846730, 75

ID: ALA3686326

PubChem CID: 87347869

Max Phase: Preclinical

Molecular Formula: C22H26F3N3O4S

Molecular Weight: 485.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NOc1ccc(C(F)(F)F)cc1C(=O)/N=c1\sc(C(C)(C)C)cn1C[C@H]1CCCO1

Standard InChI:  InChI=1S/C22H26F3N3O4S/c1-13(29)27-32-17-8-7-14(22(23,24)25)10-16(17)19(30)26-20-28(11-15-6-5-9-31-15)12-18(33-20)21(2,3)4/h7-8,10,12,15H,5-6,9,11H2,1-4H3,(H,27,29)/b26-20-/t15-/m1/s1

Standard InChI Key:  UDTOPTBWPAEPKX-XXQDRHBBSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
    5.2024   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2387   -0.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3039   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -6.1101    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -6.1100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427   -5.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -6.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5139   -6.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2694   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2704   -8.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8975   -8.1142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237   -8.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172   -8.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648   -9.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -9.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996    2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.9001    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    2.0999    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
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 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 19 20  1  0
 21 20  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 17 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  9 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3686326

   2-[(Acetylamino)oxy]-n-[(2z)-5-tert-butyl-3-[(2r)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3h)-ylidene]-5-(trifluoromethyl)benzamide

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: 485.53

Molecular Weight (Monoisotopic): 485.1596

AlogP: 4.22

#Rotatable Bonds: 5

Polar Surface Area: 81.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.34

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 3.97

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.64

Np Likeness Score: -1.15

References

1.  (2014)  Compounds as cannabinoid receptor ligands, 

Source

Source(1):

• BindingDB Database