(2R,3R,5S)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

ID: ALA3110070

Cas Number: 15386-69-3

PubChem CID: 9881867

Max Phase: Preclinical

Molecular Formula: C10H12FN5O3

Molecular Weight: 269.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)C[C@H]1O

Standard InChI:  InChI=1S/C10H12FN5O3/c11-10-14-7(12)6-8(15-10)16(3-13-6)9-5(18)1-4(2-17)19-9/h3-5,9,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,9+/m0/s1

Standard InChI Key:  PCVQISHHKVORII-OBXARNEKSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   12.9137   -6.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5904   -7.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3580   -7.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5357   -8.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2573   -7.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8642   -8.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691   -7.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8987   -7.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7062   -6.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0499   -7.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3710   -6.9217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6033   -6.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1716   -5.4270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5658   -4.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3881   -4.6801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8198   -5.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4292   -6.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1341   -3.9979    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.6457   -5.3600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  3  6  1  6
  7  8  1  0
  5  7  1  1
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 17  1  0
 12 17  1  0
 14 18  1  0
 16 19  1  0
  2 11  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3110070

   2-Fluoro-3'-deoxyadenosine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 269.24

Molecular Weight (Monoisotopic): 269.0924

AlogP: -0.81

#Rotatable Bonds: 2

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 0.76

CX LogP: -0.78

CX LogD: -0.78

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.61

Np Likeness Score: 1.10

References

1. Vodnala SK, Lundbäck T, Yeheskieli E, Sjöberg B, Gustavsson AL, Svensson R, Olivera GC, Eze AA, de Koning HP, Hammarström LG, Rottenberg ME..  (2013)  Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis.,  56  (24): [PMID:24283924] [10.1021/jm401530a]

Source

Source(1):

• Scientific Literature