(S)-3-Hydroxy-2-oxo-1-phenylpyrrolidine-3-carboxylic Acid 3-Chlorobenzylamide

ID: ALA4549484

PubChem CID: 56959669

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O3

Molecular Weight: 344.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1cccc(Cl)c1)[C@@]1(O)CCN(c2ccccc2)C1=O

Standard InChI:  InChI=1S/C18H17ClN2O3/c19-14-6-4-5-13(11-14)12-20-16(22)18(24)9-10-21(17(18)23)15-7-2-1-3-8-15/h1-8,11,24H,9-10,12H2,(H,20,22)/t18-/m0/s1

Standard InChI Key:  SKXIQDLNTUFTMU-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   18.3796  -26.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1795  -26.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671  -25.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8947  -28.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8935  -29.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6082  -30.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3246  -29.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3217  -28.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6064  -28.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5981  -27.6515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2639  -27.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0066  -26.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9294  -27.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1457  -27.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5519  -24.9995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1709  -25.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3481  -25.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9329  -24.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7286  -24.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3131  -24.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1020  -23.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3009  -23.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7199  -23.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1091  -24.4865    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
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549484

   (3S)-N-[(3-chlorophenyl)methyl]-3-hydroxy-2-oxo-1-phenylpyrrolidine-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: 344.80

Molecular Weight (Monoisotopic): 344.0928

AlogP: 2.12

#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: 1.96

CX LogD: 1.96

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: -0.99

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