Isopropyl 1,3-Dimethyl-6-[2-(methylcarbamoyl)pyridin-4-yloxy]-1H-indole-2-carboxylate

ID: ALA4084999

PubChem CID: 137647574

Max Phase: Preclinical

Molecular Formula: C21H23N3O4

Molecular Weight: 381.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(Oc2ccc3c(C)c(C(=O)OC(C)C)n(C)c3c2)ccn1

Standard InChI:  InChI=1S/C21H23N3O4/c1-12(2)27-21(26)19-13(3)16-7-6-14(11-18(16)24(19)5)28-15-8-9-23-17(10-15)20(25)22-4/h6-12H,1-5H3,(H,22,25)

Standard InChI Key:  MWOHRNDSTAAPSK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   20.0788   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8198   -3.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2969   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1182   -4.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5345   -3.3497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3557   -3.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7679   -2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7608   -4.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5232   -4.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8096   -4.7117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0559   -5.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0310   -4.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3175   -4.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6088   -4.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8912   -4.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1824   -4.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4689   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7643   -4.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7690   -3.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4784   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4872   -2.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7826   -1.9593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0691   -2.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2007   -1.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1871   -3.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6135   -3.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3270   -3.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0358   -3.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  4  9  2  0
  3 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 20 25  2  0
 16 25  1  0
 14 26  2  0
 26 27  1  0
 27 28  2  0
 12 28  1  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084999

   ---

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: 381.43

Molecular Weight (Monoisotopic): 381.1689

AlogP: 3.60

#Rotatable Bonds: 5

Polar Surface Area: 82.45

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 3.02

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.70

References

1. Kim J, Jung YK, Kim C, Shin JS, Scheers E, Lee JY, Han SB, Lee CK, Neyts J, Ha JD, Jung YS..  (2017)  A Novel Series of Highly Potent Small Molecule Inhibitors of Rhinovirus Replication.,  60  (13): [PMID:28581749] [10.1021/acs.jmedchem.7b00175]

Source

Source(1):

• Scientific Literature