(S)-3-Hydroxy-2-oxo-1-(2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyrrolidine-3-carboxylic Acid 3-Chloro-2-fluoro-benzylamide

ID: ALA4547442

PubChem CID: 89855916

Max Phase: Preclinical

Molecular Formula: C21H19ClFN3O4

Molecular Weight: 431.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCc2cc(N3CC[C@](O)(C(=O)NCc4cccc(Cl)c4F)C3=O)ccc2N1

Standard InChI:  InChI=1S/C21H19ClFN3O4/c22-15-3-1-2-13(18(15)23)11-24-19(28)21(30)8-9-26(20(21)29)14-5-6-16-12(10-14)4-7-17(27)25-16/h1-3,5-6,10,30H,4,7-9,11H2,(H,24,28)(H,25,27)/t21-/m0/s1

Standard InChI Key:  XCZMADNFSHXZKG-NRFANRHFSA-N

Molfile:  

 
     RDKit          2D

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   12.3361  -16.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7494  -14.8280    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3335  -14.0092    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9137  -14.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7845  -14.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1941  -15.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6478  -16.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9013  -16.2221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9869  -15.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4081  -14.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1936  -16.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1936  -17.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879  -17.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814  -17.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0693  -17.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613  -17.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6536  -17.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613  -16.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0693  -16.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814  -16.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4853  -16.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 11  1  0
 13 14  1  6
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 15 16  1  0
 16 17  1  0
 18 17  1  0
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 18 19  2  0
 20 17  1  0
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 23 22  2  0
 23 24  1  0
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 25 26  2  0
 27 25  1  0
 28 27  1  0
 29 28  1  0
 29 23  1  0
 30 29  2  0
 20 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547442

   (3S)-N-[(3-chloro-2-fluorophenyl)methyl]-3-hydroxy-2-oxo-1-(2-oxo-3,4-dihydro-1H-quinolin-6-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: 431.85

Molecular Weight (Monoisotopic): 431.1048

AlogP: 2.15

#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: 10.76

CX Basic pKa: ┄

CX LogP: 1.65

CX LogD: 1.65

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.05

References

1. Heinrich T, Seenisamy J, Becker F, Blume B, Bomke J, Dietz M, Eckert U, Friese-Hamim M, Gunera J, Hansen K, Leuthner B, Musil D, Pfalzgraf J, Rohdich F, Siegl C, Spuck D, Wegener A, Zenke FT..  (2019)  Identification of Methionine Aminopeptidase-2 (MetAP-2) Inhibitor M8891: A Clinical Compound for the Treatment of Cancer.,  62  (24): [PMID:31725285] [10.1021/acs.jmedchem.9b01070]

Source

Source(1):

• Scientific Literature