7-Methyl-4-(methylsulfanyl)-8-(beta-D-ribofuranosyl)-7,8-dihydropyrrolo[3',2':4,5]pyrrolo[2,3-d]pyrimidine

ID: ALA4476539

PubChem CID: 155538272

Max Phase: Preclinical

Molecular Formula: C15H18N4O4S

Molecular Weight: 350.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSc1ncnc2c1c1ccn(C)c1n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H18N4O4S/c1-18-4-3-7-9-12(16-6-17-13(9)24-2)19(14(7)18)15-11(22)10(21)8(5-20)23-15/h3-4,6,8,10-11,15,20-22H,5H2,1-2H3/t8-,10-,11-,15-/m1/s1

Standard InChI Key:  BWMKJWSKHIGHNS-ORXWAGORSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   17.4898  -11.9648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4886  -12.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1967  -13.1933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1949  -11.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9035  -11.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9083  -12.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6927  -13.0342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6849  -11.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1709  -12.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9491  -12.1045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9441  -11.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1628  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9548  -13.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4796  -14.4764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9650  -15.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7403  -14.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7338  -14.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7184  -15.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9204  -16.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4051  -15.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3912  -13.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1924  -10.7387    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4835  -10.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6131  -12.5808    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  1  0
 11 12  2  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
 10 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476539

   ---

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: 350.40

Molecular Weight (Monoisotopic): 350.1049

AlogP: 0.26

#Rotatable Bonds: 3

Polar Surface Area: 105.56

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 4.02

CX LogP: 0.78

CX LogD: 0.78

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.46

Np Likeness Score: 0.26

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