Isopropyl 7-{[2-(Methylcarbamoyl)pyridin-4-yl]oxy}-2-naphthoate

ID: ALA4086764

PubChem CID: 132022580

Max Phase: Preclinical

Molecular Formula: C21H20N2O4

Molecular Weight: 364.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(Oc2ccc3ccc(C(=O)OC(C)C)cc3c2)ccn1

Standard InChI:  InChI=1S/C21H20N2O4/c1-13(2)26-21(25)15-5-4-14-6-7-17(11-16(14)10-15)27-18-8-9-23-19(12-18)20(24)22-3/h4-13H,1-3H3,(H,22,24)

Standard InChI Key:  KXTZMMUCTWSLDY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.2957  -19.9742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2957  -20.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5866  -21.2041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8776  -20.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1685  -21.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8776  -19.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0089  -21.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7180  -20.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4271  -21.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1362  -20.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8494  -21.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5585  -20.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2676  -21.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9808  -20.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6899  -21.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3990  -20.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1081  -21.2041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1081  -22.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3990  -19.9742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6899  -22.0254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9808  -22.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2676  -22.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8494  -22.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1362  -22.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4271  -22.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7180  -22.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0089  -22.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 15 20  2  0
 20 21  1  0
 21 22  2  0
 13 22  1  0
 11 23  2  0
 23 24  1  0
 24 25  2  0
  9 25  1  0
 25 26  1  0
 26 27  2  0
  7 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086764

   ---

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: 364.40

Molecular Weight (Monoisotopic): 364.1423

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 3.03

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.64

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