(4S,7S)-4-Isobutyl-2,5,10-trioxo-17-phenyl-1-oxa-3,6,11-triazacycloheptadecane-7-carbaldehyde

ID: ALA4081590

PubChem CID: 137646911

Max Phase: Preclinical

Molecular Formula: C24H35N3O5

Molecular Weight: 445.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H]1NC(=O)OC(c2ccccc2)CCCCCNC(=O)CC[C@@H](C=O)NC1=O

Standard InChI:  InChI=1S/C24H35N3O5/c1-17(2)15-20-23(30)26-19(16-28)12-13-22(29)25-14-8-4-7-11-21(32-24(31)27-20)18-9-5-3-6-10-18/h3,5-6,9-10,16-17,19-21H,4,7-8,11-15H2,1-2H3,(H,25,29)(H,26,30)(H,27,31)/t19-,20-,21?/m0/s1

Standard InChI Key:  YBYKQGQZOOBUKJ-AHTKWCMKSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   11.6770   -8.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1208   -7.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4660   -9.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9841   -8.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8652   -8.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0793   -6.1267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1681   -8.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7666   -4.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5761   -8.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2691   -8.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7598   -9.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4660   -8.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1485   -7.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7308   -6.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7598   -8.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0378   -5.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -9.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3920   -8.2146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4099   -7.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0557   -4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -8.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7128   -6.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3678   -6.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3482   -5.9171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6066   -7.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1093   -5.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0897   -4.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9355   -5.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9360   -6.8354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8509   -4.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8313   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6316   -4.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
 18  1  1  0
 16 20  1  6
 16 14  1  0
 11 17  1  0
 22 19  1  0
 14 22  1  0
 19  2  2  0
 12  3  1  0
 19 18  1  0
  5  7  1  0
  3 11  2  0
  6 16  1  0
  7 12  1  0
 21 15  1  0
 20  8  2  0
 13  7  1  0
  4 10  1  0
 12 15  2  0
 17 21  2  0
  9  5  1  0
 10  9  1  0
 13 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 28  6  1  0
 28 29  2  0
 27 30  1  0
 30 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081590

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.56

Molecular Weight (Monoisotopic): 445.2577

AlogP: 3.02

#Rotatable Bonds: 4

Polar Surface Area: 113.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 2.56

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: 0.77

References

1. Damalanka VC, Kim Y, Galasiti Kankanamalage AC, Lushington GH, Mehzabeen N, Battaile KP, Lovell S, Chang KO, Groutas WC..  (2017)  Design, synthesis, and evaluation of a novel series of macrocyclic inhibitors of norovirus 3CL protease.,  127  [PMID:28038326] [10.1016/j.ejmech.2016.12.033]

Source

Source(1):

• Scientific Literature