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

ID: ALA4091852

PubChem CID: 137656252

Max Phase: Preclinical

Molecular Formula: C25H37N3O5

Molecular Weight: 459.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H]1NC(=O)OC(Cc2ccccc2)CCCCCNC(=O)CC[C@@H](C=O)NC1=O

Standard InChI:  InChI=1S/C25H37N3O5/c1-18(2)15-22-24(31)27-20(17-29)12-13-23(30)26-14-8-4-7-11-21(33-25(32)28-22)16-19-9-5-3-6-10-19/h3,5-6,9-10,17-18,20-22H,4,7-8,11-16H2,1-2H3,(H,26,30)(H,27,31)(H,28,32)/t20-,21?,22-/m0/s1

Standard InChI Key:  VAUXXFOKPJQVFM-NHNZYLEHSA-N

Molfile:  

     RDKit          2D

 33 34  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
    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
   11.0378   -5.7463    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
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    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
    6.7623   -9.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619  -10.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4662  -10.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1723  -10.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1692   -9.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
 15  1  1  0
 14 17  1  6
 14 13  1  0
 18 16  1  0
 13 18  1  0
 16  2  2  0
 11  3  1  0
 16 15  1  0
  5  7  1  0
  6 14  1  0
  7 11  1  0
 17  8  2  0
 12  7  1  0
  4 10  1  0
  9  5  1  0
 10  9  1  0
 12 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24  6  1  0
 24 25  2  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
  3 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091852

   ---

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: 459.59

Molecular Weight (Monoisotopic): 459.2733

AlogP: 2.89

#Rotatable Bonds: 5

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: 11.62

CX Basic pKa: ┄

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: 0.66

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