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

ID: ALA3248873

PubChem CID: 90673516

Max Phase: Preclinical

Molecular Formula: C10H14N6O5

Molecular Weight: 298.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nc(N)c2nnn([C@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C10H14N6O5/c1-20-10-12-7(11)4-8(13-10)16(15-14-4)9-6(19)5(18)3(2-17)21-9/h3,5-6,9,17-19H,2H2,1H3,(H2,11,12,13)/t3-,5-,6+,9+/m1/s1

Standard InChI Key:  XIJGUYUQEORMCN-ICKFSKTQSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   20.4805  -13.1688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0004  -13.8321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2232  -13.5774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2232  -12.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6167  -12.2165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -11.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5606  -11.1635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1670  -11.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0004  -12.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5599  -14.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5599  -14.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2232  -15.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7827  -15.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5321  -15.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3025  -14.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7827  -13.8070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4854  -14.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1131  -15.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9484  -11.4566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1754  -10.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3443  -10.0684    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA3248873

   (2S,3S,4S,5R)-2-(7-amino-5-methoxytriazolo[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: 298.26

Molecular Weight (Monoisotopic): 298.1026

AlogP: -2.58

#Rotatable Bonds: 3

Polar Surface Area: 161.66

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.42

CX Basic pKa: 0.76

CX LogP: -1.63

CX LogD: -1.63

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.47

Np Likeness Score: 0.28

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