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

ID: ALA3578060

PubChem CID: 122178228

Max Phase: Preclinical

Molecular Formula: C19H20N4O5

Molecular Weight: 384.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](NC(=O)c3c[nH]c4ccccc34)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C19H20N4O5/c1-10-8-23(19(27)22-17(10)25)16-6-14(15(9-24)28-16)21-18(26)12-7-20-13-5-3-2-4-11(12)13/h2-5,7-8,14-16,20,24H,6,9H2,1H3,(H,21,26)(H,22,25,27)/t14-,15+,16+/m0/s1

Standard InChI Key:  VLRYMVRBWXZWIG-ARFHVFGLSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   10.4236   -6.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3695   -7.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5493   -4.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -6.5858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5553   -6.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1306   -6.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7342   -8.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -5.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730   -7.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -9.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7459   -5.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3314   -8.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0899   -6.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3551   -9.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0138   -9.4453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -3.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    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  2  0
 19 24  1  0
 21 22  1  0
 22 23  1  0
 23 25  2  0
 24 23  1  0
 24 28  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3578060

   ---

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: 384.39

Molecular Weight (Monoisotopic): 384.1434

AlogP: 0.40

#Rotatable Bonds: 4

Polar Surface Area: 129.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 0.55

CX LogD: 0.54

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

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