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

ID: ALA1230628

Cas Number: 88847-89-6

PubChem CID: 135440064

Product Number: H136806, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H13N5O5

Molecular Weight: 283.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c([nH]c(=O)n2[C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1

Standard InChI:  InChI=1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3-,4+,5+/m0/s1

Standard InChI Key:  HCAJQHYUCKICQH-VPENINKCSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    1.1239    2.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239    1.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383    1.4142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383    0.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528    0.1767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239    0.1767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    0.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    1.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752    1.6692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602    1.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852    1.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752    0.3343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453   -1.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -0.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0822   -2.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -1.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752   -2.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317   -2.7414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  8  2  1  0
  4  3  1  0
  4  5  1  0
  4  6  2  0
  7  6  1  0
  7  8  2  0
  7 12  1  0
  8  9  1  0
 10  9  1  0
 10 11  2  0
 10 12  1  0
 13 12  1  6
 13 14  1  0
 13 15  1  0
 18 14  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  6
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1230628

   2'-Deoxy-7,8-dihydro-8-oxoguanosine

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: 283.24

Molecular Weight (Monoisotopic): 283.0917

AlogP: -2.36

#Rotatable Bonds: 2

Polar Surface Area: 159.25

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.34

CX Basic pKa: 0.54

CX LogP: -2.13

CX LogD: -2.43

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.41

Np Likeness Score: 0.74

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. Bertin MJ, Schwartz SL, Lee J, Korobeynikov A, Dorrestein PC, Gerwick L, Gerwick WH..  (2015)  Spongosine production by a Vibrio harveyi strain associated with the sponge Tectitethya crypta.,  78  (3): [PMID:25668560] [10.1021/np5009762]

Source

Source(1):

• Scientific Literature