(S)-3-Hydroxy-2-oxo-1-phenylpyrrolidine-3-carboxylic Acid 4-Chlorobenzylamide

ID: ALA4556838

PubChem CID: 89893318

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O3

Molecular Weight: 344.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(Cl)cc1)[C@@]1(O)CCN(c2ccccc2)C1=O

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

Standard InChI Key:  QFTHJWPUKORXPM-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   27.8318  -26.2863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6316  -26.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4194  -25.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3470  -29.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3458  -29.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0605  -30.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7767  -29.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7739  -29.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0587  -28.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0503  -27.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7162  -27.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4589  -26.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3816  -27.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5980  -27.5467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0042  -25.1203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6232  -25.4863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8004  -25.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3851  -24.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1808  -24.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7653  -24.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5542  -23.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7532  -23.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1721  -23.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1382  -23.0107    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
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556838

   (3S)-N-[(4-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: -0.83

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