(1S,2R,5S)-5-(7-Trifluoromethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-2-(2,4,5-trifluoro-phenyl)-cyclohexylamine

ID: ALA3805179

PubChem CID: 127051032

Max Phase: Preclinical

Molecular Formula: C21H19F6N5

Molecular Weight: 455.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H]1C[C@@H](N2Cc3nn4c(C(F)(F)F)ccnc4c3C2)CC[C@@H]1c1cc(F)c(F)cc1F

Standard InChI:  InChI=1S/C21H19F6N5/c22-14-7-16(24)15(23)6-12(14)11-2-1-10(5-17(11)28)31-8-13-18(9-31)30-32-19(21(25,26)27)3-4-29-20(13)32/h3-4,6-7,10-11,17H,1-2,5,8-9,28H2/t10-,11+,17-/m0/s1

Standard InChI Key:  AJGKSIDNLVRWTM-RVPKQNPDSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    9.9329    4.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5414    3.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3304    2.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5113    1.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9028    2.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1137    3.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391    1.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7306    0.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7569    2.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9236    4.0628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8474    1.4084    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5968    4.7390    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7318    0.3704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    1.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -1.9215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -1.0186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225    1.5280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810    1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -1.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2269    4.0816    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6247   -2.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8301   -3.6855    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8007   -3.0254    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0059   -3.9242    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  3  1  1
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
  5 14  1  0
  2 15  1  0
 10 16  1  6
 16 17  1  0
 17 20  1  0
 19 18  1  0
 18 16  1  0
 19 20  1  0
 20 23  2  0
 22 21  1  0
 21 19  2  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
  6 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805179

   ---

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: 455.41

Molecular Weight (Monoisotopic): 455.1545

AlogP: 4.14

#Rotatable Bonds: 2

Polar Surface Area: 59.45

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.57

CX LogP: 3.38

CX LogD: 1.26

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -0.70

References

1. Cox JM, Chu HD, Kuethe JT, Gao YD, Scapin G, Eiermann G, He H, Li X, Lyons KA, Metzger J, Petrov A, Wu JK, Xu S, Sinha-Roy R, Weber AE, Biftu T..  (2016)  The discovery of novel 5,6,5- and 5,5,6-tricyclic pyrrolidines as potent and selective DPP-4 inhibitors.,  26  (11): [PMID:27106708] [10.1016/j.bmcl.2016.04.020]

Source

Source(1):

• Scientific Literature