9-alpha-D-Arabinofuranosyl-2-methylsulfonyl-8-azaadenine

ID: ALA3248872

PubChem CID: 90673515

Max Phase: Preclinical

Molecular Formula: C10H14N6O6S

Molecular Weight: 346.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1nc(N)c2nnn([C@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C10H14N6O6S/c1-23(20,21)10-12-7(11)4-8(13-10)16(15-14-4)9-6(19)5(18)3(2-17)22-9/h3,5-6,9,17-19H,2H2,1H3,(H2,11,12,13)/t3-,5-,6+,9+/m1/s1

Standard InChI Key:  LDVSSMISRNGKLG-ICKFSKTQSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.0610  -13.3670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5809  -14.0302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8036  -13.7755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8036  -12.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1972  -12.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638  -11.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1410  -11.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7475  -11.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5809  -12.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1404  -14.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1404  -15.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8036  -15.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3631  -15.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1126  -16.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8830  -14.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3631  -14.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0658  -14.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6935  -15.3919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5288  -11.6548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7559  -11.0660    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.9248  -10.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0428  -10.6565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1707  -11.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 10 16  1  0
 10  3  1  6
  8 19  1  0
  6 20  1  0
 20 21  1  0
 20 22  2  0
 20 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3248872

   (2S,3S,4S,5R)-2-(7-amino-5-methylsulfonyltriazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol

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: 346.33

Molecular Weight (Monoisotopic): 346.0696

AlogP: -3.18

#Rotatable Bonds: 3

Polar Surface Area: 186.57

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.42

CX Basic pKa: ┄

CX LogP: -2.63

CX LogD: -2.63

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 0.04

References

1. Montgomery JA, Shortnacy AT, Arnett G, Shannon WM..  (1977)  2-Substituted derivatives of 9-alpha-D-arabinofuranosyladenine and 9-alpha-D-arabinofuranosyl-8-azaadenine.,  20  (3): [PMID:191611] [10.1021/jm00213a017]

Source

Source(1):

• Scientific Literature