US8785477, Sitagliptin

ID: ALA3185489

Cas Number: 823817-56-7

PubChem CID: 11306691

Product Number: R335956, Order Now?

Max Phase: Preclinical

Molecular Formula: C16H15F6N5O

Molecular Weight: 407.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F

Standard InChI:  InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2

Standard InChI Key:  MFFMDFFZMYYVKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.9336   -3.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 N   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 N   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
   -2.7248   -1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 N   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
   -3.1875    2.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611    2.8890    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    3.5299    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5575    3.7800    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4886   -5.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -6.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8268   -5.4110    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8267   -8.1110    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -8.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -8.1109    0.0000 F   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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 20  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3185489

   rac-Sitagliptin

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: 407.32

Molecular Weight (Monoisotopic): 407.1181

AlogP: 2.02

#Rotatable Bonds: 4

Polar Surface Area: 77.04

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.78

CX LogP: 1.26

CX LogD: -0.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -1.40

References

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

2. Vivesh, Kaur B, Jaglan S, Rani S, Batra Y, Singh P..  (2022)  Proline based rationally designed peptide esters against dipeptidyl peptidase-4: Highly potent anti-diabetic agents.,  76  [PMID:36209967] [10.1016/j.bmcl.2022.129018]

Source

Source(2):

• Scientific Literature
• BindingDB Database