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

ID: ALA3248874

PubChem CID: 90673517

Max Phase: Preclinical

Molecular Formula: C9H14N8O4

Molecular Weight: 298.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NNc1nc(N)c2nnn([C@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C9H14N8O4/c10-6-3-7(13-9(12-6)14-11)17(16-15-3)8-5(20)4(19)2(1-18)21-8/h2,4-5,8,18-20H,1,11H2,(H3,10,12,13,14)/t2-,4-,5+,8+/m1/s1

Standard InChI Key:  MIKWZLKNGOTMSR-UZJDFGQCSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    7.1290  -20.6969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6488  -21.3602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8716  -21.1055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8716  -20.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651  -19.7446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4318  -18.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2090  -18.6915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8155  -19.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6488  -20.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083  -21.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083  -22.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8716  -22.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311  -22.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806  -23.4347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510  -21.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311  -21.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1338  -21.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615  -22.7219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5968  -18.9847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8238  -18.3960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928  -17.5965    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  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3248874

   (2S,3S,4S,5R)-2-(7-amino-5-hydrazinyltriazolo[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): 298.1138

AlogP: -3.30

#Rotatable Bonds: 3

Polar Surface Area: 190.48

Molecular Species: NEUTRAL

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.42

CX Basic pKa: 7.14

CX LogP: -2.08

CX LogD: -2.27

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.25

Np Likeness Score: -0.03

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