(2R,3R,4R,5R)-5-(acetoxymethyl)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-2-cyanotetrahydrofuran-3,4-diyl diacetate

ID: ALA4875811

PubChem CID: 145074481

Max Phase: Preclinical

Molecular Formula: C18H19N5O7

Molecular Weight: 417.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@](C#N)(c2ccc3c(N)ncnn23)[C@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C18H19N5O7/c1-9(24)27-6-13-15(28-10(2)25)16(29-11(3)26)18(7-19,30-13)14-5-4-12-17(20)21-8-22-23(12)14/h4-5,8,13,15-16H,6H2,1-3H3,(H2,20,21,22)/t13-,15-,16-,18+/m1/s1

Standard InChI Key:  CFRUKNYMDAGASC-IIVZCXTMSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   42.0789   -5.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6706   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3329   -6.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4123   -6.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6261   -7.5588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5914   -6.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0039   -5.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3388   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5540   -5.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3822   -4.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1056   -7.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.5756   -5.4127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.2876   -5.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2876   -4.1793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.5756   -3.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8635   -5.0043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8635   -4.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0790   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5940   -4.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5756   -2.9376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.9929   -6.5652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5974   -4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2852   -7.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4233   -7.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6374   -8.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0061   -7.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.9506   -6.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7994   -8.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4255   -3.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9845   -5.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  4  5  1  6
  6  4  1  0
  4  2  1  0
  2  7  1  0
  7  8  1  0
  8  6  1  0
  8  9  1  1
  9 10  1  0
  6 11  1  6
 17 15  1  0
 16 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  1  2  0
  1 16  1  0
 15 20  1  0
  3 21  3  0
 10 22  1  0
 11 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 23 27  2  0
 23 28  1  0
 22 29  2  0
 22 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875811

   ---

Molecule Features

Natural Product: No

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: 417.38

Molecular Weight (Monoisotopic): 417.1284

AlogP: -0.14

#Rotatable Bonds: 5

Polar Surface Area: 168.13

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.65

CX LogP: -0.56

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: 0.44

References

1. Mackman RL, Hui HC, Perron M, Murakami E, Palmiotti C, Lee G, Stray K, Zhang L, Goyal B, Chun K, Byun D, Siegel D, Simonovich S, Du Pont V, Pitts J, Babusis D, Vijjapurapu A, Lu X, Kim C, Zhao X, Chan J, Ma B, Lye D, Vandersteen A, Wortman S, Barrett KT, Toteva M, Jordan R, Subramanian R, Bilello JP, Cihlar T..  (2021)  Prodrugs of a 1'-CN-4-Aza-7,9-dideazaadenosine C-Nucleoside Leading to the Discovery of Remdesivir (GS-5734) as a Potent Inhibitor of Respiratory Syncytial Virus with Efficacy in the African Green Monkey Model of RSV.,  64  (8.0): [PMID:33835812] [10.1021/acs.jmedchem.1c00071]

Source

Source(1):

• Scientific Literature