(E/Z)-N-((S)-1-(((S)-4-Chloro-4-cyano-1-((S)-2-oxopiperidin-3-yl)but-3-en-2-yl)amino)-3-(4-fluorophenyl)-1-oxopropan-2-yl)-5-methylisoxazole-3-carboxamide

ID: ALA4515394

PubChem CID: 155539814

Max Phase: Preclinical

Molecular Formula: C24H25ClFN5O4

Molecular Weight: 501.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)N[C@@H](Cc2ccc(F)cc2)C(=O)N[C@H](C=C(Cl)C#N)C[C@@H]2CCCNC2=O)no1

Standard InChI:  InChI=1S/C24H25ClFN5O4/c1-14-9-21(31-35-14)24(34)30-20(10-15-4-6-18(26)7-5-15)23(33)29-19(12-17(25)13-27)11-16-3-2-8-28-22(16)32/h4-7,9,12,16,19-20H,2-3,8,10-11H2,1H3,(H,28,32)(H,29,33)(H,30,34)/t16-,19-,20-/m0/s1

Standard InChI Key:  GXXOKWOOOJLTBM-VDGAXYAQSA-N

Molfile:  

 
     RDKit          2D

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   31.9255  -13.5344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4950  -13.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2102  -14.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   34.0699  -16.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.1885  -13.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7402  -13.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2659  -11.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.2171  -10.7362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4978  -11.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2209  -12.7080    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.7815  -10.7362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 22 23  1  0
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 22 25  1  0
 17 26  1  0
 27 26  1  1
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 28 29  1  0
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 31 32  1  0
 19 33  1  0
 32 34  2  0
 20 35  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4515394

   ---

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: 501.95

Molecular Weight (Monoisotopic): 501.1579

AlogP: 2.51

#Rotatable Bonds: 9

Polar Surface Area: 137.12

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.39

CX Basic pKa: ┄

CX LogP: 2.03

CX LogD: 2.03

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.45

Np Likeness Score: -0.72

References

1. Ma Y, Li L, He S, Shang C, Sun Y, Liu N, Meek TD, Wang Y, Shang L..  (2019)  Application of Dually Activated Michael Acceptor to the Rational Design of Reversible Covalent Inhibitor for Enterovirus 71 3C Protease.,  62  (13): [PMID:31184893] [10.1021/acs.jmedchem.9b00387]

Source

Source(1):

• Scientific Literature