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

ID: ALA4783620

PubChem CID: 143139086

Max Phase: Preclinical

Molecular Formula: C23H30N4O5

Molecular Weight: 442.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)c1cc2ccccc2[nH]1)C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)CO

Standard InChI:  InChI=1S/C23H30N4O5/c1-13(2)9-18(27-23(32)19-10-14-5-3-4-6-16(14)25-19)22(31)26-17(20(29)12-28)11-15-7-8-24-21(15)30/h3-6,10,13,15,17-18,25,28H,7-9,11-12H2,1-2H3,(H,24,30)(H,26,31)(H,27,32)/t15-,17-,18-/m0/s1

Standard InChI Key:  KGHYEZHKSVQRJH-SZMVWBNQSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   26.3718  -19.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7887  -19.9913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7803  -18.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6016  -18.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0060  -17.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0144  -19.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8357  -19.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2526  -19.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2442  -18.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8274  -17.8438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5933  -17.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2359  -17.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0572  -17.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4616  -16.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4700  -17.8341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8190  -16.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2275  -15.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0412  -15.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2064  -14.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4921  -14.4097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8840  -14.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0792  -14.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4036  -15.7000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.2829  -16.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5505  -19.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0657  -18.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0735  -19.9567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2909  -19.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2900  -18.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5810  -18.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8724  -18.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8772  -19.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5868  -20.1182    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
M  END

Alternative Forms

1. Parent:

   

   ALA4783620

   ---

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: 442.52

Molecular Weight (Monoisotopic): 442.2216

AlogP: 0.88

#Rotatable Bonds: 10

Polar Surface Area: 140.39

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.65

CX Basic pKa: ┄

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: 0.21

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