N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]-methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide

ID: ALA4756136

PubChem CID: 70331453

Max Phase: Preclinical

Molecular Formula: C25H34N4O6

Molecular Weight: 486.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc2[nH]c(C(=O)N[C@@H](CC(C)(C)C)C(=O)N[C@@H](C[C@@H]3CCNC3=O)C(=O)CO)cc12

Standard InChI:  InChI=1S/C25H34N4O6/c1-25(2,3)12-19(24(34)28-17(20(31)13-30)10-14-8-9-26-22(14)32)29-23(33)18-11-15-16(27-18)6-5-7-21(15)35-4/h5-7,11,14,17,19,27,30H,8-10,12-13H2,1-4H3,(H,26,32)(H,28,34)(H,29,33)/t14-,17-,19-/m0/s1

Standard InChI Key:  CEMUHRBVCDSEOL-FNHZYXHNSA-N

Molfile:  

 
     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
   10.9957  -10.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4147  -11.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4062  -10.2162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2317  -10.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6382   -9.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6466  -10.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4721  -10.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8911  -11.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8827  -10.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4636   -9.4886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2234   -8.7805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8743   -8.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6998   -8.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1062   -8.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1147   -9.4790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4553   -8.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8659   -7.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6837   -7.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8497   -6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1318   -6.0371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5206   -6.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7117   -6.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0378   -7.3340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9317   -8.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1702  -10.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6828  -10.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6908  -11.6124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9041  -11.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9033  -10.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1907  -10.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4785  -10.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4833  -11.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965  -11.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1889   -9.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4767   -8.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2905  -10.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  6
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  1  0
  5 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 21 22  2  0
 17 23  1  6
 14 24  1  0
  1 25  1  0
 25 26  2  0
 26 29  1  0
 28 27  1  0
 27 25  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 30 34  1  0
 34 35  1  0
  7 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756136

   N-[(2S)-1-[[(2S)-4-hydroxy-3-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]amino]-4,4-dimethyl-1-oxopentan-2-yl]-4-methoxy-1H-indole-2-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: 486.57

Molecular Weight (Monoisotopic): 486.2478

AlogP: 1.28

#Rotatable Bonds: 10

Polar Surface Area: 149.62

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.50

CX Basic pKa: ┄

CX LogP: 0.62

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.34

Np Likeness Score: 0.20

References

1. Hoffman RL,Kania RS,Brothers MA,Davies JF,Ferre RA,Gajiwala KS,He M,Hogan RJ,Kozminski K,Li LY,Lockner JW,Lou J,Marra MT,Mitchell LJ,Murray BW,Nieman JA,Noell S,Planken SP,Rowe T,Ryan K,Smith GJ,Solowiej JE,Steppan CM,Taggart B.  (2020)  Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19.,  63  (21): [PMID:33054210] [10.1021/acs.jmedchem.0c01063]

Source

Source(1):

• Scientific Literature