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

ID: ALA1688964

Cas Number: 3868-31-3

PubChem CID: 135407175

Product Number: H303620, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H13N5O6

Molecular Weight: 299.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 8-Hydroxyguanosine

Canonical SMILES:  Nc1nc2c(nc(O)n2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1

Standard InChI Key:  FPGSEBKFEJEOSA-UMMCILCDSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   24.3140   -7.8921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0257   -7.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0257   -6.6585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3140   -6.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6022   -7.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6023   -6.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8133   -6.3974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3256   -7.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8133   -7.7397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5565   -8.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7718   -8.7773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7717   -9.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5565   -9.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0413   -9.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8663   -9.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8114  -10.6419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1043  -10.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3506   -9.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5006   -7.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3160   -5.4170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7396   -7.8968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  5  6  2  0
  6  4  1  0
  5  1  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 10  9  1  1
  1  2  2  0
 14 15  1  6
  2  3  1  0
 13 16  1  6
  6  7  1  0
 12 17  1  1
  7  8  2  0
 17 18  1  0
  8  9  1  0
  8 19  1  0
  9  5  1  0
  4 20  2  0
 10 11  1  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1688964

   8-Hydroxyguanosine

Molecule Features

Natural Product: Yes

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: 299.24

Molecular Weight (Monoisotopic): 299.0866

AlogP: -2.98

#Rotatable Bonds: 2

Polar Surface Area: 179.74

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.10

CX Basic pKa: ┄

CX LogP: -2.33

CX LogD: -2.33

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.34

Np Likeness Score: 0.89

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]

2. Alvarez Z, Lee K, Abel-Santos E..  (2010)  Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.,  54  (12): [PMID:20921305] [10.1128/aac.01029-10]

Source

Source(1):

• Scientific Literature