US9238658, 5

ID: ALA3957689

PubChem CID: 89612826

Max Phase: Preclinical

Molecular Formula: C21H21FN4O3

Molecular Weight: 396.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cccc(NC(=O)N2CCC(c3noc4ccc(F)cc34)CC2)c1

Standard InChI:  InChI=1S/C21H21FN4O3/c1-23-20(27)14-3-2-4-16(11-14)24-21(28)26-9-7-13(8-10-26)19-17-12-15(22)5-6-18(17)29-25-19/h2-6,11-13H,7-10H2,1H3,(H,23,27)(H,24,28)

Standard InChI Key:  ANGSQFFGSKRQFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -5.1231  -13.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4092  -12.1639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8501  -11.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7166  -12.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2080  -10.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6475   -9.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0022   -8.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9173   -7.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4777   -7.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3902   -6.7589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9504   -7.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -8.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -6.1485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233   -6.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327   -3.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -4.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    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
   -2.3383    1.3500    0.0000 F   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
   -6.1231   -9.2507    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  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  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  2  0
 29  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3957689

   4-(5-fluoro-1,2-benzoxazol-3-yl)-N-[3-(methylcarbamoyl)phenyl]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: 396.42

Molecular Weight (Monoisotopic): 396.1598

AlogP: 3.74

#Rotatable Bonds: 3

Polar Surface Area: 87.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.05

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -1.95

References

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

Source

Source(1):

• BindingDB Database