ethyl 4-(3-(2-((2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl)-2-oxoethylamino)-3-methylbutanoyl)piperazine-1-carboxylate

ID: ALA1085597

PubChem CID: 44218555

Max Phase: Preclinical

Molecular Formula: C19H30FN5O4

Molecular Weight: 411.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)N1CCN(C(=O)CC(C)(C)NCC(=O)N2C[C@@H](F)C[C@H]2C#N)CC1

Standard InChI:  InChI=1S/C19H30FN5O4/c1-4-29-18(28)24-7-5-23(6-8-24)16(26)10-19(2,3)22-12-17(27)25-13-14(20)9-15(25)11-21/h14-15,22H,4-10,12-13H2,1-3H3/t14-,15-/m0/s1

Standard InChI Key:  GULFOOMFOLZGEA-GJZGRUSLSA-N

Molfile:  

     RDKit          2D

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    0.6477   -7.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -6.6934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662   -7.8551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664   -7.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -7.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943   -7.3706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -8.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9573   -7.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4884   -7.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521   -6.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2515   -6.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1579   -8.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -9.2753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -6.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9208   -6.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7747   -7.9223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620   -5.5794    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -7.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2019   -7.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159   -8.7295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065   -9.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7831   -8.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366   -9.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6446   -8.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9494   -9.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -9.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0862   -8.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 14  1  1
  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
 18 20  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
  1  2  1  0
 18 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 10 11  1  0
 22 25  1  0
 11 12  1  0
 25 26  1  0
 12 13  1  0
 25 27  2  0
 13  8  1  0
 26 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085597

   ethyl 4-(3-(2-((2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl)-2-oxoethylamino)-3-methylbutanoyl)piperazine-1-carboxylate

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: 411.48

Molecular Weight (Monoisotopic): 411.2282

AlogP: 0.51

#Rotatable Bonds: 6

Polar Surface Area: 105.98

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.41

CX LogP: -1.07

CX LogD: -2.13

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.89

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