(S)-1-(4-Carbamoylphenyl)-3-hydroxy-2-oxopyrrolidine-3-carboxylic Acid 3-Chloro-5-fluorobenzylamide

ID: ALA4536649

PubChem CID: 89893272

Max Phase: Preclinical

Molecular Formula: C19H17ClFN3O4

Molecular Weight: 405.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc(N2CC[C@](O)(C(=O)NCc3cc(F)cc(Cl)c3)C2=O)cc1

Standard InChI:  InChI=1S/C19H17ClFN3O4/c20-13-7-11(8-14(21)9-13)10-23-17(26)19(28)5-6-24(18(19)27)15-3-1-12(2-4-15)16(22)25/h1-4,7-9,28H,5-6,10H2,(H2,22,25)(H,23,26)/t19-/m0/s1

Standard InChI Key:  DNBZUYUEKSXSFF-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   15.1894   -4.7159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9893   -4.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7770   -4.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7045   -7.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7034   -8.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4181   -8.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1345   -8.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1316   -7.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4163   -7.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4080   -6.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0738   -5.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8166   -4.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7393   -5.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9555   -5.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3618   -3.5499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9808   -3.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1580   -3.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7428   -3.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5385   -3.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1231   -2.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9119   -2.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1110   -1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5298   -2.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9192   -3.0369    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.8968   -1.0118    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.4179   -9.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7034   -9.9177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1321   -9.9181    0.0000 O   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
  6 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536649

   (3S)-1-(4-carbamoylphenyl)-N-[(3-chloro-5-fluorophenyl)methyl]-3-hydroxy-2-oxopyrrolidine-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: 405.81

Molecular Weight (Monoisotopic): 405.0892

AlogP: 1.36

#Rotatable Bonds: 5

Polar Surface Area: 112.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.76

CX Basic pKa: ┄

CX LogP: 0.96

CX LogD: 0.95

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -1.22

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