US8846730, 63

ID: ALA3686340

PubChem CID: 91808092

Max Phase: Preclinical

Molecular Formula: C29H38F3N3O5S

Molecular Weight: 597.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cn(C[C@H]2CCCO2)/c(=N/C(=O)c2cc(C(F)(F)F)ccc2OCCC/N=C/OC2CCCCO2)s1

Standard InChI:  InChI=1S/C29H38F3N3O5S/c1-28(2,3)24-18-35(17-21-8-6-14-37-21)27(41-24)34-26(36)22-16-20(29(30,31)32)10-11-23(22)38-15-7-12-33-19-40-25-9-4-5-13-39-25/h10-11,16,18-19,21,25H,4-9,12-15,17H2,1-3H3/b33-19+,34-27-/t21-,25?/m1/s1

Standard InChI Key:  IMTUOFVITGCQSJ-WGJXSQJOSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  1  0  0  0  0  0999 V2000
    8.6082   -4.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4148   -4.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7092   -5.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9024   -5.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054   -3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5554   -1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5517   -0.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8550    0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2794    1.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7162    2.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2162    2.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6857    1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4759    0.1843    0.0000 O   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024   -2.6977    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
   -0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   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
   -2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109   -7.4996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9117   -8.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148   -9.7490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156  -10.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2209  -11.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5225  -12.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8189  -11.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8138  -10.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121   -9.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0388    3.6015    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394    3.6005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006    4.2008    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.3382   -2.9741    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 31  1  0
 20 37  1  0
 37 38  1  0
 37 39  1  0
 37 40  1  0
 14 41  1  0
 41  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3686340

   oxan-2-yl N-[3-[2-[[5-tert-butyl-3-[[(2R)-oxolan-2-yl]methyl]-1,3-thiazol-2-ylidene]carbamoyl]-4-(trifluoromethyl)phenoxy]propyl]methanimidate

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: 597.70

Molecular Weight (Monoisotopic): 597.2484

AlogP: 6.13

#Rotatable Bonds: 10

Polar Surface Area: 83.64

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 3.60

CX LogP: 5.69

CX LogD: 5.69

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.19

Np Likeness Score: -0.90

References

1.  (2014)  Compounds as cannabinoid receptor ligands, 

Source

Source(1):

• BindingDB Database