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

ID: ALA606057

PubChem CID: 135976314

Max Phase: Preclinical

Molecular Formula: C10H14N6O6

Molecular Weight: 314.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2nc(NO)n(C3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C10H14N6O6/c11-9-13-6-3(7(20)14-9)12-10(15-21)16(6)8-5(19)4(18)2(1-17)22-8/h2,4-5,8,17-19,21H,1H2,(H,12,15)(H3,11,13,14,20)/t2-,4-,5-,8?/m1/s1

Standard InChI Key:  RSXBCNVKGMXLHG-BKKZJBRMSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.2292   -1.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -0.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -2.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -2.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -1.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -2.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -1.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -3.4125    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  2  1  0
  6  3  2  0
  7  2  2  0
  8  4  1  0
  9 12  2  0
 10  4  1  0
 11  5  2  0
 12  7  1  0
 13  8  1  0
 14 10  1  0
 15  3  1  0
  8 16  1  6
 17 12  1  0
 18 11  1  0
 13 19  1  6
 14 20  1  1
 21 15  1  0
 22 20  1  0
  6  5  1  0
 14 13  1  0
 11  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA606057

   ---

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: 314.26

Molecular Weight (Monoisotopic): 314.0975

AlogP: -2.47

#Rotatable Bonds: 3

Polar Surface Area: 192.03

Molecular Species: NEUTRAL

HBA: 12

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.46

CX Basic pKa: 0.55

CX LogP: -1.52

CX LogD: -1.52

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.30

Np Likeness Score: 0.72

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