(S)-1-(2-Cyanophenyl)-3-hydroxy-2-oxopyrrolidine-3-carboxylic Acid 3-Chloro-5-fluorobenzylamide

ID: ALA4529723

PubChem CID: 89893263

Max Phase: Preclinical

Molecular Formula: C19H15ClFN3O3

Molecular Weight: 387.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccccc1N1CC[C@](O)(C(=O)NCc2cc(F)cc(Cl)c2)C1=O

Standard InChI:  InChI=1S/C19H15ClFN3O3/c20-14-7-12(8-15(21)9-14)11-23-17(25)19(27)5-6-24(18(19)26)16-4-2-1-3-13(16)10-22/h1-4,7-9,27H,5-6,11H2,(H,23,25)/t19-/m0/s1

Standard InChI Key:  DUJJENQXRPYECK-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

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    1.8655  -26.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649  -26.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527  -25.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804  -29.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792  -30.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0936  -30.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8095  -30.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067  -29.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0918  -28.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834  -28.0681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490  -27.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918  -26.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4150  -27.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317  -27.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373  -25.4173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6569  -25.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8330  -25.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176  -25.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2129  -25.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7972  -24.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5861  -23.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855  -23.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047  -24.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5929  -24.9046    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5714  -22.8805    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208  -28.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2333  -28.4691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  1  0
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  2 13  1  0
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  9 10  1  0
 13 14  2  0
  3 15  1  0
  3 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 20 24  1  0
 22 25  1  0
 26 27  3  0
  8 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529723

   (3S)-N-[(3-chloro-5-fluorophenyl)methyl]-1-(2-cyanophenyl)-3-hydroxy-2-oxopyrrolidine-3-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 387.80

Molecular Weight (Monoisotopic): 387.0786

AlogP: 2.13

#Rotatable Bonds: 4

Polar Surface Area: 93.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.75

CX Basic pKa: ┄

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -1.26

References

1. Heinrich T, Seenisamy J, Blume B, Bomke J, Calderini M, Eckert U, Friese-Hamim M, Kohl R, Lehmann M, Leuthner B, Musil D, Rohdich F, Zenke FT..  (2019)  Discovery and Structure-Based Optimization of Next-Generation Reversible Methionine Aminopeptidase-2 (MetAP-2) Inhibitors.,  62  (10): [PMID:30939017] [10.1021/acs.jmedchem.9b00041]

Source

Source(1):

• Scientific Literature