(S)-3-Hydroxy-2-oxo-1-phenylpyrrolidine-3-carboxylic Acid 3,5-Difluorobenzylamide

ID: ALA4558399

PubChem CID: 56960816

Max Phase: Preclinical

Molecular Formula: C18H16F2N2O3

Molecular Weight: 346.33

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H16F2N2O3/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:  QCMLCNXMSHSKMM-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   27.6694   -4.3158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4692   -4.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2569   -3.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1845   -7.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1834   -7.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8980   -8.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6143   -7.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6114   -7.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8962   -6.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8879   -5.8017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5537   -5.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2965   -4.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2191   -5.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4355   -5.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8417   -3.1498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4608   -3.5158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6379   -3.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2227   -2.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0184   -3.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6029   -2.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3917   -1.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5908   -1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0097   -1.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3989   -2.6368    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.3766   -0.6119    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
 20 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558399

   (3S)-N-[(3,5-difluorophenyl)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: 346.33

Molecular Weight (Monoisotopic): 346.1129

AlogP: 1.75

#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: 1.64

CX LogD: 1.64

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.93

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