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

ID: ALA4556036

PubChem CID: 89893288

Max Phase: Preclinical

Molecular Formula: C18H17FN2O3

Molecular Weight: 328.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1F)[C@@]1(O)CCN(c2ccccc2)C1=O

Standard InChI:  InChI=1S/C18H17FN2O3/c19-15-9-5-4-6-13(15)12-20-16(22)18(24)10-11-21(17(18)23)14-7-2-1-3-8-14/h1-9,24H,10-12H2,(H,20,22)/t18-/m0/s1

Standard InChI Key:  IQELGVVHVJRQOZ-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   37.3799  -26.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1798  -26.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9674  -25.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8951  -28.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8938  -29.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6086  -30.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3248  -29.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3220  -28.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6068  -28.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5984  -27.7431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.2642  -27.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0070  -26.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9297  -27.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1460  -27.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5522  -25.0911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1713  -25.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3484  -25.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9332  -24.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7289  -24.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3133  -24.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1023  -23.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3012  -23.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7202  -23.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9389  -25.7408    0.0000 F   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
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556036

   (3S)-N-[(2-fluorophenyl)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: 328.34

Molecular Weight (Monoisotopic): 328.1223

AlogP: 1.61

#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: 1.50

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -1.05

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