3-(2-((2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl)-2-oxoethylamino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide

ID: ALA1085305

PubChem CID: 46890912

Max Phase: Preclinical

Molecular Formula: C20H27FN4O4

Molecular Weight: 406.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)CC(C)(C)NCC(=O)N2C[C@@H](F)C[C@H]2C#N)cc1OC

Standard InChI:  InChI=1S/C20H27FN4O4/c1-20(2,23-11-19(27)25-12-13(21)7-15(25)10-22)9-18(26)24-14-5-6-16(28-3)17(8-14)29-4/h5-6,8,13,15,23H,7,9,11-12H2,1-4H3,(H,24,26)/t13-,15-/m0/s1

Standard InChI Key:  VQNOMKDKYPNXAG-ZFWWWQNUSA-N

Molfile:  

     RDKit          2D

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    3.3313   -1.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -0.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -1.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499   -1.4593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1782   -1.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783   -0.9749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060   -2.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1725   -0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7361    0.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9354   -0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -2.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0442   -2.8798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6046   -0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -1.5266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0462    0.8165    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992   -1.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107   -0.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019    0.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184   -0.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255   -1.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839   -1.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165    0.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1929    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327    0.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -0.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0
 14 15  3  0
  4 16  1  0
  2  4  1  0
  4 17  1  0
  4  5  1  0
  1 18  1  0
  5  6  1  0
 12 19  1  1
  6  7  1  0
 18 20  1  0
  7  8  1  0
 20 21  2  0
  7  9  2  0
 21 22  1  0
  8 10  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 10 11  1  0
 24 25  2  0
 25 20  1  0
 11 12  1  0
 12 13  1  0
 26 27  1  0
 22 26  1  0
 13  8  1  0
 10 14  1  1
 28 29  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085305

   3-(2-((2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl)-2-oxoethylamino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide

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: 406.46

Molecular Weight (Monoisotopic): 406.2016

AlogP: 1.86

#Rotatable Bonds: 8

Polar Surface Area: 103.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.41

CX LogP: 0.35

CX LogD: -0.70

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.87

References

1. Yeh TK, Tsai TY, Hsu T, Cheng JH, Chen X, Song JS, Shy HS, Chiou MC, Chien CH, Tseng YJ, Huang CY, Yeh KC, Huang YL, Huang CH, Huang YW, Wang MH, Tang HK, Chao YS, Chen CT, Jiaang WT..  (2010)  (2S,4S)-1-[2-(1,1-dimethyl-3-oxo-3-pyrrolidin-1-yl-propylamino)acetyl]-4-fluoro-pyrrolidine-2-carbonitrile: a potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV.,  20  (12): [PMID:20483603] [10.1016/j.bmcl.2010.04.124]

Source

Source(1):

• Scientific Literature