US9238658, 9

ID: ALA3942485

PubChem CID: 89612908

Max Phase: Preclinical

Molecular Formula: C23H23FN4O2S

Molecular Weight: 438.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1nc2ccc(NC(=O)N3CCC(c4noc5ccc(F)cc45)CC3)cc2s1

Standard InChI:  InChI=1S/C23H23FN4O2S/c1-2-3-21-26-18-6-5-16(13-20(18)31-21)25-23(29)28-10-8-14(9-11-28)22-17-12-15(24)4-7-19(17)30-27-22/h4-7,12-14H,2-3,8-11H2,1H3,(H,25,29)

Standard InChI Key:  VANSFYQPKNRCRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    2.3952   -6.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -5.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -4.4224    0.0000 C   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
    2.4133   -1.7530    0.0000 N   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
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4994    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7985    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7985    2.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    3.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    2.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0982    3.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2341    5.2246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7009    5.5385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4520    4.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9197    3.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3852    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3831    1.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7555    0.2484    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9154    1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4499    3.1249    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
    0.3114   -2.9665    0.0000 S   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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 19  1  0
 28 22  1  0
  9 29  1  0
 29 30  2  0
 30  6  1  0
 30 31  1  0
 31  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3942485

   4-(5-fluoro-1,2-benzoxazol-3-yl)-N-(2-propyl-1,3-benzothiazol-6-yl)piperidine-1-carboxamide

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: 438.53

Molecular Weight (Monoisotopic): 438.1526

AlogP: 5.94

#Rotatable Bonds: 4

Polar Surface Area: 71.26

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.00

CX Basic pKa: 2.84

CX LogP: 4.66

CX LogD: 4.66

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -2.34

References

1.  (2016)  Substituted piperidinyl-carboxamide derivatives useful as SCD 1 inhibitors, 

Source

Source(1):

• BindingDB Database