N-((2S,3S,5R)-2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-6-methoxy-2-naphthamide

ID: ALA3578050

PubChem CID: 122178218

Max Phase: Preclinical

Molecular Formula: C22H23N3O6

Molecular Weight: 425.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc(C(=O)N[C@H]3C[C@H](n4cc(C)c(=O)[nH]c4=O)O[C@@H]3CO)ccc2c1

Standard InChI:  InChI=1S/C22H23N3O6/c1-12-10-25(22(29)24-20(12)27)19-9-17(18(11-26)31-19)23-21(28)15-4-3-14-8-16(30-2)6-5-13(14)7-15/h3-8,10,17-19,26H,9,11H2,1-2H3,(H,23,28)(H,24,27,29)/t17-,18+,19+/m0/s1

Standard InChI Key:  FJDJXRYOJFDRHT-IPMKNSEASA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -6.1731   10.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496    9.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3425    5.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9988    1.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8097    5.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049    3.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5599    4.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8909    7.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    3.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4199    6.9200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6672    6.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8598    1.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4254    9.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    8.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8294   10.8730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3960    8.5994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067    3.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494    0.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9326   -0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5 10  1  1
  8 11  2  0
  9 12  1  1
 14 10  1  0
 10  8  1  0
  6  9  1  0
 12  4  1  0
 13  2  1  0
  3  5  1  0
 13 15  2  0
  9  7  1  0
  2 14  2  0
  6  3  1  0
  8 16  1  0
 16 13  1  0
  2  1  1  0
  5  7  1  0
  6 17  1  6
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 19 25  1  0
 21 22  1  0
 22 23  2  0
 24 25  2  0
 24 29  1  0
 23 24  1  0
 23 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 27 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3578050

   ---

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: 425.44

Molecular Weight (Monoisotopic): 425.1587

AlogP: 1.09

#Rotatable Bonds: 5

Polar Surface Area: 122.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 1.28

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: 0.01

References

1. Vernekar SK, Qiu L, Zhang J, Kankanala J, Li H, Geraghty RJ, Wang Z..  (2015)  5'-Silylated 3'-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus.,  58  (9): [PMID:25909386] [10.1021/acs.jmedchem.5b00327]

Source

Source(1):

• Scientific Literature