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

ID: ALA4556165

PubChem CID: 134229916

Max Phase: Preclinical

Molecular Formula: C14H17N5O4

Molecular Weight: 319.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1ccc2c1c1c(N)ncnc1n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H17N5O4/c1-18-3-2-6-9(18)8-12(15)16-5-17-13(8)19(6)14-11(22)10(21)7(4-20)23-14/h2-3,5,7,10-11,14,20-22H,4H2,1H3,(H2,15,16,17)/t7-,10-,11-,14-/m1/s1

Standard InChI Key:  ITDRXDTWCNITTA-FRJWGUMJSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   12.8219  -18.3868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8207  -19.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5288  -19.6153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5270  -17.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2356  -18.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2404  -19.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0248  -19.4561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0170  -18.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5030  -18.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2812  -18.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2762  -17.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4949  -17.4581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2869  -20.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8117  -20.8984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2971  -21.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0724  -21.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659  -20.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2375  -16.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0505  -22.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2525  -22.5110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7372  -21.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7233  -19.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5246  -17.1607    0.0000 N   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
 12 18  1  0
 15 19  1  1
 19 20  1  0
 16 21  1  6
 17 22  1  6
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556165

   ---

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: 319.32

Molecular Weight (Monoisotopic): 319.1281

AlogP: -0.88

#Rotatable Bonds: 2

Polar Surface Area: 131.58

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 6.15

CX LogP: -0.93

CX LogD: -0.95

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: 0.70

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