4-(6-fluoroindolin-1-yl)-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)piperidine-1-carboxamide

ID: ALA3093879

PubChem CID: 71657443

Max Phase: Preclinical

Molecular Formula: C21H25FN4OS

Molecular Weight: 400.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2c(s1)CCCC2)N1CCC(N2CCc3ccc(F)cc32)CC1

Standard InChI:  InChI=1S/C21H25FN4OS/c22-15-6-5-14-7-12-26(18(14)13-15)16-8-10-25(11-9-16)21(27)24-20-23-17-3-1-2-4-19(17)28-20/h5-6,13,16H,1-4,7-12H2,(H,23,24,27)

Standard InChI Key:  MAOIZDNDCRXLFG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    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
    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 C   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
   -2.7248   -1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1884   -2.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -3.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9781   -4.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -5.5536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537   -5.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0990   -3.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2452   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3962   -7.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1582   -8.0475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101   -9.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343  -10.6289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3218  -11.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003  -13.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9362  -14.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3936  -14.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8152  -12.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793  -11.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926  -10.0550    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  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  9  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 20  2  0
 25 26  1  0
 26 18  1  0
  8 27  1  0
 27  5  1  0
 27 28  2  0
 28  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3093879

   4-(6-fluoro-2,3-dihydroindol-1-yl)-N-(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: 400.52

Molecular Weight (Monoisotopic): 400.1733

AlogP: 4.22

#Rotatable Bonds: 2

Polar Surface Area: 48.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.87

CX Basic pKa: 2.68

CX LogP: 4.23

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.82

Np Likeness Score: -2.16

References

1. Yang SM, Tang Y, Zhang R, Lu H, Kuo GH, Gaul MD, Li Y, Ho G, Conway JG, Liang Y, Lenhard JM, Demarest KT, Murray WV..  (2013)  4-Bicyclic heteroaryl-piperidine derivatives as potent, orally bioavailable Stearoyl-CoA desaturase-1 (SCD1) inhibitors. Part 1: urea-based analogs.,  23  (24): [PMID:24153205] [10.1016/j.bmcl.2013.09.096]

2.  (2016)  Substituted piperidinyl-carboxamide derivatives useful as SCD 1 inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database