(S)-1-(4-Cyanophenyl)-3-hydroxy-2-oxopyrrolidine-3-carboxylic Acid 3-Chloro-5-fluorobenzylamide

ID: ALA4559822

PubChem CID: 89893264

Max Phase: Preclinical

Molecular Formula: C19H15ClFN3O3

Molecular Weight: 387.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(N2CC[C@](O)(C(=O)NCc3cc(F)cc(Cl)c3)C2=O)cc1

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

Standard InChI Key:  SVXAGSRVOWQLDP-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

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   18.3677  -26.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1676  -26.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9552  -25.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8828  -28.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8817  -29.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5964  -30.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3127  -29.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3098  -28.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5946  -28.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5863  -27.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2521  -27.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9949  -26.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9175  -27.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1338  -27.3268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5400  -24.9003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1591  -25.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3362  -25.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9211  -24.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7168  -24.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3013  -24.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0901  -23.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2892  -23.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7081  -23.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0973  -24.3873    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0750  -22.3623    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.5992  -30.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5990  -31.6766    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
 12  2  1  0
  2 13  1  0
 13 10  1  0
  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
  6 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559822

   (3S)-N-[(3-chloro-5-fluorophenyl)methyl]-1-(4-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: -1.43

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