US8785477, Vildagliptin

ID: ALA3665969

Cas Number: 1360862-63-0

PubChem CID: 5251896

Max Phase: Preclinical

Molecular Formula: C17H25N3O2

Molecular Weight: 303.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC1CCCN1C(=O)CNC12CC3CC(CC(O)(C3)C1)C2

Standard InChI:  InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2

Standard InChI Key:  SYOKIDBDQMKNDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    1.6421   -1.2737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600   -1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -1.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -1.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000   -2.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -2.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400   -1.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -0.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4900   -0.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.1627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293    1.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    3.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1546    4.0227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758    4.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5510    3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5093    4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081    6.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545    5.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947    6.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8343    7.4639    0.0000 N   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  1  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10  4  1  0
  9 11  1  0
 11  2  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 20 21  1  0
 21 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3665969

   1-[2-[(3-Hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile

Molecule Features

Natural Product: Yes

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: 303.41

Molecular Weight (Monoisotopic): 303.1947

AlogP: 1.17

#Rotatable Bonds: 3

Polar Surface Area: 76.36

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.03

CX LogP: -0.22

CX LogD: -1.85

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -0.50

References

1.  (2014)  Hexahydropyrrolo[3,4-b]pyrrole derivatives, preparation methods and pharmaceutical uses thereof, 

Source

Source(1):

• BindingDB Database