US8895592, 36

ID: ALA3647333

PubChem CID: 46834664

Max Phase: Preclinical

Molecular Formula: C21H22F3N3O3S

Molecular Weight: 453.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1/c(=N/C(=O)c2cc(C(F)(F)F)ccc2OC[C@H](C)O)sc2ncccc21

Standard InChI:  InChI=1S/C21H22F3N3O3S/c1-3-4-10-27-16-6-5-9-25-19(16)31-20(27)26-18(29)15-11-14(21(22,23)24)7-8-17(15)30-12-13(2)28/h5-9,11,13,28H,3-4,10,12H2,1-2H3/b26-20-/t13-/m0/s1

Standard InChI Key:  ALPMIDBDCVDTKH-XQUWXSQBSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
   -0.8533   -7.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -6.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -4.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -4.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -3.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -5.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591   -7.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -8.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3092   -8.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0591   -7.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3090   -5.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0621   -4.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5629   -4.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3160   -3.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7178   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5160   -3.1226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -9.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -9.6140    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6592  -10.6522    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594  -10.6528    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 S   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 N   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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 12 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  6 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  5  1  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3647333

   N-(1-butyl-[1,3]thiazolo[5,4-b]pyridin-2-ylidene)-2-[(2S)-2-hydroxypropoxy]-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: 453.49

Molecular Weight (Monoisotopic): 453.1334

AlogP: 4.42

#Rotatable Bonds: 7

Polar Surface Area: 76.71

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.57

CX LogP: 4.56

CX LogD: 4.56

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -1.64

References

1.  (2014)  Compounds as cannabinoid receptor ligands, 

Source

Source(1):

• BindingDB Database