US8895592, 1

ID: ALA3647300

PubChem CID: 46833218

Max Phase: Preclinical

Molecular Formula: C24H34BrN3O2S

Molecular Weight: 508.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cn1cc(C(C)(C)C)s/c1=N\C(=O)c1cc(Br)ccc1OC[C@@H]1CCCN1C

Standard InChI:  InChI=1S/C24H34BrN3O2S/c1-16(2)13-28-14-21(24(3,4)5)31-23(28)26-22(29)19-12-17(25)9-10-20(19)30-15-18-8-7-11-27(18)6/h9-10,12,14,16,18H,7-8,11,13,15H2,1-6H3/b26-23-/t18-/m0/s1

Standard InChI Key:  RPSJSJZDPRLONT-RHGYLGJDSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
    8.5223    2.2429    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
    9.1760    0.2701    0.0000 C   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
    6.5517   -0.8722    0.0000 N   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
    6.8054   -3.2859    0.0000 C   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
    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
    0.0000    2.7000    0.0000 Br  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
   -0.0934   -6.1101    0.0000 C   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
   -3.6595   -5.7324    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
    8.6082   -4.7808    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
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 13  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  6
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 26 27  1  0
  7 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3647300

   5-bromo-N-[5-tert-butyl-3-(2-methylpropyl)-1,3-thiazol-2-ylidene]-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]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: 508.53

Molecular Weight (Monoisotopic): 507.1555

AlogP: 5.48

#Rotatable Bonds: 6

Polar Surface Area: 46.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.91

CX LogP: 6.03

CX LogD: 5.40

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -1.12

References

1.  (2014)  Compounds as cannabinoid receptor ligands, 

Source

Source(1):

• BindingDB Database