(2R,4R)-4-fluoro-1-(2-(4-methyl-1-(methylsulfonyl)piperidin-4-ylamino)acetyl)pyrrolidine-2-carbonitrile

ID: ALA456419

PubChem CID: 44590649

Max Phase: Preclinical

Molecular Formula: C14H23FN4O3S

Molecular Weight: 346.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(NCC(=O)N2C[C@H](F)C[C@@H]2C#N)CCN(S(C)(=O)=O)CC1

Standard InChI:  InChI=1S/C14H23FN4O3S/c1-14(3-5-18(6-4-14)23(2,21)22)17-9-13(20)19-10-11(15)7-12(19)8-16/h11-12,17H,3-7,9-10H2,1-2H3/t11-,12-/m1/s1

Standard InChI Key:  ZPUILNOHDOBYOB-VXGBXAGGSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.0590  -10.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759  -10.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7809   -9.7277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879  -10.9695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047  -10.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8146  -11.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4745  -11.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6546  -11.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -9.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -8.9112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8827  -12.5803    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470  -10.5441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3520   -9.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -9.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764   -8.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662   -8.0733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -8.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389   -9.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333  -10.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743   -7.2484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -6.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1993   -7.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -7.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 12  1  0
  2  4  1  0
 12 13  1  0
 13 14  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  4  5  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
  9 10  3  0
 16 20  1  0
  5  9  1  1
 20 21  1  0
  2  3  2  0
 20 22  2  0
  7 11  1  1
 20 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA456419

   (2R,4R)-4-fluoro-1-(2-(4-methyl-1-(methylsulfonyl)piperidin-4-ylamino)acetyl)pyrrolidine-2-carbonitrile

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: 346.43

Molecular Weight (Monoisotopic): 346.1475

AlogP: -0.15

#Rotatable Bonds: 4

Polar Surface Area: 93.51

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.04

CX LogP: -2.15

CX LogD: -3.79

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -0.69

References

1. Havale SH, Pal M..  (2009)  Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.,  17  (5): [PMID:19217790] [10.1016/j.bmc.2009.01.061]

Source

Source(1):

• Scientific Literature