(S)-3-Hydroxy-2-oxo-1-phenylpyrrolidine-3-carboxylic Acid 3-Chloro-5-fluorobenzylamide

ID: ALA4552396

PubChem CID: 89893711

Max Phase: Preclinical

Molecular Formula: C18H16ClFN2O3

Molecular Weight: 362.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1cc(F)cc(Cl)c1)[C@@]1(O)CCN(c2ccccc2)C1=O

Standard InChI:  InChI=1S/C18H16ClFN2O3/c19-13-8-12(9-14(20)10-13)11-21-16(23)18(25)6-7-22(17(18)24)15-4-2-1-3-5-15/h1-5,8-10,25H,6-7,11H2,(H,21,23)/t18-/m0/s1

Standard InChI Key:  GYXUHDDOWYYRFT-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   36.8092   -4.4699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6090   -4.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3967   -3.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3243   -7.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3232   -8.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0379   -8.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7541   -8.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7513   -7.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0361   -6.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0277   -5.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6936   -5.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4363   -4.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3590   -5.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5753   -5.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9816   -3.3039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6006   -3.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7776   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3625   -2.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1581   -3.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7426   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5315   -1.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7306   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1495   -2.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5164   -0.7660    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.5387   -2.7910    0.0000 Cl  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
 22 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552396

   (3~{S})-~{N}-[(3-chloranyl-5-fluoranyl-phenyl)methyl]-3-oxidanyl-2-oxidanylidene-1-phenyl-pyrrolidine-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: 362.79

Molecular Weight (Monoisotopic): 362.0833

AlogP: 2.26

#Rotatable Bonds: 4

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.76

CX Basic pKa: ┄

CX LogP: 2.10

CX LogD: 2.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: -1.18

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