(2S,3R,4S,5R)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA4580420

Cas Number: 77691-03-3

PubChem CID: 494271

Max Phase: Preclinical

Molecular Formula: C11H14N4O4

Molecular Weight: 266.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c[nH]c12

Standard InChI:  InChI=1S/C11H14N4O4/c12-11-7-6(14-3-15-11)4(1-13-7)10-9(18)8(17)5(2-16)19-10/h1,3,5,8-10,13,16-18H,2H2,(H2,12,14,15)/t5-,8-,9-,10+/m1/s1

Standard InChI Key:  KEHFJRVBOUROMM-KBHCAIDQSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   36.7860   -3.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8178   -2.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0419   -2.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3691   -2.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9647   -3.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7088   -2.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4818   -3.9993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9989   -2.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0072   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8844   -1.5029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0661   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1444   -2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4871   -2.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5791   -3.5730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3274   -3.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9847   -3.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8937   -2.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5500   -2.1135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2654   -3.9966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1
  1  3  1  0
  4  3  1  0
  5  1  1  0
  6  4  1  0
  5  7  1  6
  6  8  1  1
  9  8  1  0
  5  6  1  0
  2 13  1  0
 12 10  1  0
 10 11  1  0
 11  2  2  0
 12 13  2  0
 12 17  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  1 19  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4580420

   D-Ribitol, 1-C-(4-amino-5H-pyrrolo(3,2-D)pyrimidin-7-yl)-1,4-anhydro-, (S)-

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 266.26

Molecular Weight (Monoisotopic): 266.1015

AlogP: -1.31

#Rotatable Bonds: 2

Polar Surface Area: 137.51

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.59

CX Basic pKa: 4.54

CX LogP: -1.83

CX LogD: -1.83

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.45

Np Likeness Score: 1.29

References

1. Brai A, Martelli F, Riva V, Garbelli A, Fazi R, Zamperini C, Pollutri A, Falsitta L, Ronzini S, Maccari L, Maga G, Giannecchini S, Botta M..  (2019)  DDX3X Helicase Inhibitors as a New Strategy To Fight the West Nile Virus Infection.,  62  (5): [PMID:30721061] [10.1021/acs.jmedchem.8b01403]

Source

Source(1):

• Scientific Literature