Ethyl 3-Hydroxy-7-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}-2-naphthoate

ID: ALA4103185

PubChem CID: 132022623

Max Phase: Preclinical

Molecular Formula: C20H18N2O5

Molecular Weight: 366.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2cc(Oc3ccnc(C(=O)NC)c3)ccc2cc1O

Standard InChI:  InChI=1S/C20H18N2O5/c1-3-26-20(25)16-9-13-8-14(5-4-12(13)10-18(16)23)27-15-6-7-22-17(11-15)19(24)21-2/h4-11,23H,3H2,1-2H3,(H,21,24)

Standard InChI Key:  SFHASDYGRQYHKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   28.3018  -12.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3018  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5928  -13.7323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8878  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1787  -13.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0068  -13.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7159  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4250  -13.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1341  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8390  -13.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5481  -13.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2531  -13.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9622  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6713  -13.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3804  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0853  -13.7323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0853  -14.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3804  -12.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6713  -14.5495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9622  -14.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2531  -14.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8390  -14.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1341  -14.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4250  -14.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7159  -14.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0068  -14.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3018  -14.9581    0.0000 O   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
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 14 19  2  0
 19 20  1  0
 20 21  2  0
 12 21  1  0
 10 22  2  0
 22 23  1  0
 23 24  2  0
  8 24  1  0
 24 25  1  0
 25 26  2  0
  6 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103185

   ---

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: 366.37

Molecular Weight (Monoisotopic): 366.1216

AlogP: 3.27

#Rotatable Bonds: 5

Polar Surface Area: 97.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: 3.03

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -0.44

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