4-Methoxy-8-(beta-D-ribofuranosyl)-8H-furo[2',3':4,5]pyrrolo[2,3-d]pyrimidine

ID: ALA4483740

PubChem CID: 134229894

Max Phase: Preclinical

Molecular Formula: C14H15N3O6

Molecular Weight: 321.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ncnc2c1c1occc1n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H15N3O6/c1-21-13-8-11-6(2-3-22-11)17(12(8)15-5-16-13)14-10(20)9(19)7(4-18)23-14/h2-3,5,7,9-10,14,18-20H,4H2,1H3/t7-,9-,10-,14-/m1/s1

Standard InChI Key:  PGAUOMHMEJHMTO-AKAIJSEGSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   17.6920   -3.0871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6909   -3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3989   -4.3156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3971   -2.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1057   -3.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1106   -3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8949   -4.1565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8871   -2.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3731   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1513   -3.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1463   -2.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3650   -2.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1570   -4.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6818   -5.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1672   -6.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9425   -5.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9361   -5.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9207   -7.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1227   -7.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6073   -6.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5934   -4.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3947   -1.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6858   -1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 13  7  1  1
 15 18  1  1
 18 19  1  0
 16 20  1  6
 17 21  1  6
  4 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483740

   ---

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: 321.29

Molecular Weight (Monoisotopic): 321.0961

AlogP: -0.20

#Rotatable Bonds: 3

Polar Surface Area: 123.00

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 4.38

CX LogP: -0.42

CX LogD: -0.42

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: 0.64

References

1. Tokarenko A, Lišková B, Smoleń S, Táborská N, Tichý M, Gurská S, Perlíková P, Frydrych I, Tloušt'ová E, Znojek P, Mertlíková-Kaiserová H, Poštová Slavětínská L, Pohl R, Klepetářová B, Khalid NU, Wenren Y, Laposa RR, Džubák P, Hajdúch M, Hocek M..  (2018)  Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and Furo-Fused 7-Deazapurine Ribonucleosides.,  61  (20): [PMID:30281308] [10.1021/acs.jmedchem.8b01258]

Source

Source(1):

• Scientific Literature