[1-(S)-1-cyclohexyl-2-oxo-(3,3,4,4,tetrafluoropyrrolidin-1-yl)ethyl]amine

ID: ALA380860

PubChem CID: 9838664

Max Phase: Preclinical

Molecular Formula: C12H18F4N2O

Molecular Weight: 282.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)N1CC(F)(F)C(F)(F)C1)C1CCCCC1

Standard InChI:  InChI=1S/C12H18F4N2O/c13-11(14)6-18(7-12(11,15)16)10(19)9(17)8-4-2-1-3-5-8/h8-9H,1-7,17H2/t9-/m0/s1

Standard InChI Key:  QAXKYHMZAQHVBK-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -5.5179   -8.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5179   -8.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8034   -9.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -8.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -8.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8034   -7.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8046   -6.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0907   -6.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5195   -6.4263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3758   -6.8358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918   -5.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855   -7.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4784   -7.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0669   -7.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -6.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -7.5252    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4849   -6.5260    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -8.6526    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6865   -8.0384    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  8 10  1  0
  3  4  1  0
  8 11  2  0
 10 12  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
  1  2  1  0
 14 16  1  0
  7  8  1  0
 14 17  1  0
  1  6  1  0
 13 18  1  0
  7  9  1  6
 13 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA380860

   (S)-2-amino-2-cyclohexyl-1-(3,3,4,4-tetrafluoropyrrolidin-1-yl)ethanone

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: 282.28

Molecular Weight (Monoisotopic): 282.1355

AlogP: 2.01

#Rotatable Bonds: 2

Polar Surface Area: 46.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.49

CX LogP: 2.05

CX LogD: 0.93

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.79

Np Likeness Score: 0.06

References

1. Wright SW, Ammirati MJ, Andrews KM, Brodeur AM, Danley DE, Doran SD, Lillquist JS, McClure LD, McPherson RK, Orena SJ, Parker JC, Polivkova J, Qiu X, Soeller WC, Soglia CB, Treadway JL, VanVolkenburg MA, Wang H, Wilder DC, Olson TV..  (2006)  cis-2,5-dicyanopyrrolidine inhibitors of dipeptidyl peptidase IV: synthesis and in vitro, in vivo, and X-ray crystallographic characterization.,  49  (11): [PMID:16722626] [10.1021/jm0600085]

2. Lu IL, Tsai KC, Chiang YK, Jiaang WT, Wu SH, Mahindroo N, Chien CH, Lee SJ, Chen X, Chao YS, Wu SY..  (2008)  A three-dimensional pharmacophore model for dipeptidyl peptidase IV inhibitors.,  43  (8): [PMID:18207285] [10.1016/j.ejmech.2007.11.014]

Source

Source(1):

• Scientific Literature