US9238658, 60

ID: ALA3918573

PubChem CID: 117728500

Max Phase: Preclinical

Molecular Formula: C20H21FN4O3S

Molecular Weight: 416.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2c(s1)CC(O)CC2)N1CCC(c2noc3ccc(F)cc23)CC1

Standard InChI:  InChI=1S/C20H21FN4O3S/c21-12-1-4-16-14(9-12)18(24-28-16)11-5-7-25(8-6-11)20(27)23-19-22-15-3-2-13(26)10-17(15)29-19/h1,4,9,11,13,26H,2-3,5-8,10H2,(H,22,23,27)

Standard InChI Key:  VBTAHQJOCMSDHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    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
   -2.7248    1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -0.0031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8532   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2514   -2.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3541   -1.3071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1041   -2.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6041   -2.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3542   -1.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6042   -0.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1042   -0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8549   -1.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7131   -0.0926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1403   -0.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1421   -2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2582   -3.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9484   -4.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5224   -4.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2746   -6.1628    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4063   -3.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7162   -2.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    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
    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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 11  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 17  1  0
 26 20  1  0
  7 27  1  0
 27 28  1  0
 28  5  2  0
 28 29  1  0
 29  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3918573

   4-(5-fluoro-1,2-benzoxazol-3-yl)-N-(6-hydroxy-4,5,6,7-tetrahydro-1,3-benzothiazol-2-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: 416.48

Molecular Weight (Monoisotopic): 416.1318

AlogP: 3.68

#Rotatable Bonds: 2

Polar Surface Area: 91.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.85

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.75

References

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

Source

Source(1):

• BindingDB Database