(S)-3-Hydroxy-2-oxo-1-(2-oxo-2,3-dihydro-1H-indol-5-yl)pyrrolidine-3-carboxylic Acid 3-Chloro-5-fluorobenzylamide

ID: ALA4524329

PubChem CID: 89855890

Max Phase: Preclinical

Molecular Formula: C20H17ClFN3O4

Molecular Weight: 417.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1Cc2cc(N3CC[C@](O)(C(=O)NCc4cc(F)cc(Cl)c4)C3=O)ccc2N1

Standard InChI:  InChI=1S/C20H17ClFN3O4/c21-13-5-11(6-14(22)9-13)10-23-18(27)20(29)3-4-25(19(20)28)15-1-2-16-12(7-15)8-17(26)24-16/h1-2,5-7,9,29H,3-4,8,10H2,(H,23,27)(H,24,26)/t20-/m0/s1

Standard InChI Key:  ORZFRLILCIPIFT-FQEVSTJZSA-N

Molfile:  

 
     RDKit          2D

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   28.9075   -5.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6952   -4.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3262   -6.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9921   -5.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7348   -5.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6575   -5.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8738   -6.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2801   -3.6789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8990   -4.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   31.4567   -3.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0413   -2.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8302   -2.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0291   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4480   -2.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8374   -3.1659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.8150   -1.1409    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.3304   -7.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6156   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6177   -8.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0437   -7.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0493   -8.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3371   -8.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5179   -9.6122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3419   -9.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6702   -8.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7621  -10.3997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  2  0
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 24 23  2  0
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  4 20  1  0
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 26 27  1  0
 27 28  1  0
 28 24  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524329

   (3S)-N-[(3-chloro-5-fluorophenyl)methyl]-3-hydroxy-2-oxo-1-(2-oxo-1,3-dihydroindol-5-yl)pyrrolidine-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: 417.82

Molecular Weight (Monoisotopic): 417.0892

AlogP: 1.76

#Rotatable Bonds: 4

Polar Surface Area: 98.74

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.74

CX Basic pKa: ┄

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.20

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