2-Amino-8-azido-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one

ID: ALA604396

PubChem CID: 135976320

Max Phase: Preclinical

Molecular Formula: C10H12N8O5

Molecular Weight: 324.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=Nc1nc2c(O)nc(N)nc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H12N8O5/c11-9-14-6-3(7(22)15-9)13-10(16-17-12)18(6)8-5(21)4(20)2(1-19)23-8/h2,4-5,8,19-21H,1H2,(H3,11,14,15,22)/t2-,4-,5-,8?/m1/s1

Standard InChI Key:  YSFMXIULKVUVMD-BKKZJBRMSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.5167   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    0.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -0.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417    0.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -1.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875    0.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042    0.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250    0.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -2.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -0.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042    1.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -3.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  2  2  0
  7  3  2  0
  8  4  1  0
  9 13  2  0
 10  4  1  0
 11  5  2  0
 12  2  1  0
 13  7  1  0
 14 12  2  0
 15  8  1  0
 16 10  1  0
 17 14  2  0
  8 18  1  6
 19 13  1  0
 20 11  1  0
 15 21  1  6
 16 22  1  1
 23 22  1  0
  6  5  1  0
 16 15  1  0
 11  9  1  0
M  CHG  2  14   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA604396

   ---

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: 324.26

Molecular Weight (Monoisotopic): 324.0931

AlogP: -1.33

#Rotatable Bonds: 3

Polar Surface Area: 208.53

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -13.99

CX Basic pKa: ┄

CX LogP: -0.61

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.26

Np Likeness Score: 0.73

References

1. Lin TS, Cheng JC, Ishiguro K, Sartorelli AC..  (1985)  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.,  28  (9): [PMID:3861870] [10.1021/jm00147a012]

Source

Source(1):

• Scientific Literature