US9238658, 7

ID: ALA3919582

PubChem CID: 89612771

Max Phase: Preclinical

Molecular Formula: C23H23FN4O3

Molecular Weight: 422.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1nc2ccc(NC(=O)N3CCC(c4noc5ccc(F)cc45)CC3)cc2o1

Standard InChI:  InChI=1S/C23H23FN4O3/c1-2-3-21-26-18-6-5-16(13-20(18)30-21)25-23(29)28-10-8-14(9-11-28)22-17-12-15(24)4-7-19(17)31-27-22/h4-7,12-14H,2-3,8-11H2,1H3,(H,25,29)

Standard InChI Key:  ZVWKGLGQTXILAQ-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 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
   -0.0031    3.0008    0.0000 N   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
   -2.3421    3.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061    6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080    6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    9.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   10.6092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5540   12.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   12.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553   13.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5230   12.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9885   11.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1626   11.1708    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9863   10.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187   10.6124    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
    0.3114   -2.9665    0.0000 N   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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 18  1  0
 27 21  1  0
  8 28  2  0
 28 29  1  0
 29 30  2  0
 30  6  1  0
 30 31  1  0
 31  4  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3919582

   4-(5-fluoro-1,2-benzoxazol-3-yl)-N-(2-propyl-1,3-benzoxazol-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: 422.46

Molecular Weight (Monoisotopic): 422.1754

AlogP: 5.47

#Rotatable Bonds: 4

Polar Surface Area: 84.40

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.79

CX Basic pKa: 0.86

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.99

References

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

Source

Source(1):

• BindingDB Database