(S)-N4-tert-butyl-N1-(2-(2-fluorobenzamido)ethyl)-2-(5-methylisoxazole-3-sulfonamido)succinamide

ID: ALA4548705

PubChem CID: 155549227

Max Phase: Preclinical

Molecular Formula: C21H28FN5O6S

Molecular Weight: 497.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(S(=O)(=O)N[C@@H](CC(=O)NC(C)(C)C)C(=O)NCCNC(=O)c2ccccc2F)no1

Standard InChI:  InChI=1S/C21H28FN5O6S/c1-13-11-18(26-33-13)34(31,32)27-16(12-17(28)25-21(2,3)4)20(30)24-10-9-23-19(29)14-7-5-6-8-15(14)22/h5-8,11,16,27H,9-10,12H2,1-4H3,(H,23,29)(H,24,30)(H,25,28)/t16-/m0/s1

Standard InChI Key:  GQWNRFHXIIMDAV-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   32.0892  -10.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6847  -10.1984    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.2758  -10.9015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1004  -10.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.1004  -11.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9772   -9.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8081  -11.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8081  -12.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   37.3466  -10.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0543   -9.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3466  -11.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7609  -10.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4682   -9.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4686   -8.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7559   -8.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0516   -8.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3424   -8.5722    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.8877   -8.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0886   -8.8104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6800   -9.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2266  -10.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8673   -9.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  6 18  1  0
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 24 25  1  0
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 10 30  2  0
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 33 10  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548705

   ---

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: 497.55

Molecular Weight (Monoisotopic): 497.1744

AlogP: 0.62

#Rotatable Bonds: 10

Polar Surface Area: 159.50

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.72

CX Basic pKa: ┄

CX LogP: 0.27

CX LogD: 0.13

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: -1.66

References

1. Zhan W, Visone J, Ouellette T, Harris JC, Wang R, Zhang H, Singh PK, Ginn J, Sukenick G, Wong TT, Okoro JI, Scales RM, Tumwebaze PK, Rosenthal PJ, Kafsack BFC, Cooper RA, Meinke PT, Kirkman LA, Lin G..  (2019)  Improvement of Asparagine Ethylenediamines as Anti-malarial Plasmodium-Selective Proteasome Inhibitors.,  62  (13): [PMID:31177777] [10.1021/acs.jmedchem.9b00363]

Source

Source(1):

• Scientific Literature