(2R,3S,5R)-5-(2-cyclopropyl-6H-pyrrolo[3,4-d]pyrimidin-6-yl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-amine

ID: ALA2425062

PubChem CID: 72188906

Max Phase: Preclinical

Molecular Formula: C20H19F3N4O

Molecular Weight: 388.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H]1C[C@@H](n2cc3cnc(C4CC4)nc3c2)CO[C@@H]1c1cc(F)c(F)cc1F

Standard InChI:  InChI=1S/C20H19F3N4O/c21-14-5-16(23)15(22)4-13(14)19-17(24)3-12(9-28-19)27-7-11-6-25-20(10-1-2-10)26-18(11)8-27/h4-8,10,12,17,19H,1-3,9,24H2/t12-,17+,19-/m1/s1

Standard InChI Key:  JHKIZAUXJSBIHB-JLBUNGTFSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    3.9979  -14.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967  -14.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7048  -15.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4144  -14.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4116  -14.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030  -13.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005  -12.8643    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901  -13.6819    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7046  -16.1360    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1205  -15.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1198  -16.1342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8241  -16.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5336  -16.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5342  -15.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8254  -14.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2440  -16.5425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3277  -17.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9913  -16.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5368  -16.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1235  -17.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5269  -18.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3434  -18.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7548  -17.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3491  -16.8232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5720  -17.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250  -14.0881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2765  -17.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2780  -17.1192    0.0000 C   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
  6  7  1  0
  1  8  1  0
  3  9  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10  4  1  6
 16 17  1  0
 17 20  2  0
 19 18  2  0
 18 16  1  0
 13 16  1  1
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 23 25  1  0
 15 26  1  1
 27 25  1  0
 28 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425062

   (2R,3S,5R)-5-(2-cyclopropylpyrrolo[3,4-d]pyrimidin-6-yl)-2-(2,4,5-trifluorophenyl)oxan-3-amine

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: 388.39

Molecular Weight (Monoisotopic): 388.1511

AlogP: 3.76

#Rotatable Bonds: 3

Polar Surface Area: 65.96

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.11

CX LogP: 3.25

CX LogD: 1.54

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -0.57

References

1. Biftu T, Qian X, Chen P, Feng D, Scapin G, Gao YD, Cox J, Roy RS, Eiermann G, He H, Lyons K, Salituro G, Patel S, Petrov A, Xu F, Xu SS, Zhang B, Caldwell C, Wu JK, Lyons K, Weber AE..  (2013)  Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2- (2,5-difluorophenyl)-5-(4,6-dihydropyrrolo [3,4-c]pyrazol-5-(1H)-yl)tetrahydro-2H-pyran-3-amine (23) [corrected].,  23  (19): [PMID:23972441] [10.1016/j.bmcl.2013.07.061]

Source

Source(1):

• Scientific Literature