(2S,3S,4S,5R)-2-(7-amino-5-azido-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA3248875

PubChem CID: 90673518

Max Phase: Preclinical

Molecular Formula: C9H11N9O4

Molecular Weight: 309.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=Nc1nc(N)c2nnn([C@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C9H11N9O4/c10-6-3-7(13-9(12-6)15-16-11)18(17-14-3)8-5(21)4(20)2(1-19)22-8/h2,4-5,8,19-21H,1H2,(H2,10,12,13)/t2-,4-,5+,8+/m1/s1

Standard InChI Key:  LTGGCZPNJHQWNN-UZJDFGQCSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   14.4631  -17.4942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9829  -18.1575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2057  -17.9028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2057  -17.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5992  -16.5419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7658  -15.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5431  -15.4888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1495  -16.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9829  -16.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5424  -18.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5424  -19.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2057  -19.6803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7652  -19.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5146  -20.2320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2850  -18.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7652  -18.1324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4679  -18.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0956  -19.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9309  -15.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1579  -15.1933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1506  -14.3751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1464  -13.5579    0.0000 N   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  2  0
 21 22  2  0
M  CHG  2  21   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3248875

   (2S,3S,4S,5R)-2-(7-amino-5-azidotriazolo[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: 309.25

Molecular Weight (Monoisotopic): 309.0934

AlogP: -1.64

#Rotatable Bonds: 3

Polar Surface Area: 201.19

Molecular Species: ACID

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -15.71

CX Basic pKa: 0.05

CX LogP: -1.05

CX LogD: -1.16

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.29

Np Likeness Score: 0.41

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