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

ID: ALA3578056

PubChem CID: 122178224

Max Phase: Preclinical

Molecular Formula: C21H21N3O5

Molecular Weight: 395.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](NC(=O)c3cccc4ccccc34)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C21H21N3O5/c1-12-10-24(21(28)23-19(12)26)18-9-16(17(11-25)29-18)22-20(27)15-8-4-6-13-5-2-3-7-14(13)15/h2-8,10,16-18,25H,9,11H2,1H3,(H,22,27)(H,23,26,28)/t16-,17+,18+/m0/s1

Standard InChI Key:  YDNKMXQEKQXYHX-RCCFBDPRSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -7.8162    9.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343    9.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7896    6.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9584    6.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3176    7.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    5.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176    7.5371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6797   10.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626    6.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1925    8.7654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   10.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569    5.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1207   11.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6707    8.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8916   11.9790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6434   11.3192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    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
   -0.2489    3.5938    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
   -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
    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
  5 10  1  6
  8 11  2  0
  9 12  1  6
 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  1
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 19 25  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 29  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3578056

   ---

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: 395.42

Molecular Weight (Monoisotopic): 395.1481

AlogP: 1.08

#Rotatable Bonds: 4

Polar Surface Area: 113.42

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 1.44

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -0.09

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