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

ID: ALA3143095

PubChem CID: 135407735

Max Phase: Preclinical

Molecular Formula: C11H15N5O5

Molecular Weight: 297.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nc2c(O)nc(N)nc2n1[C@H]1C[C@H](O)[C@@H](CO)O1

Standard InChI:  InChI=1S/C11H15N5O5/c1-20-11-13-7-8(14-10(12)15-9(7)19)16(11)6-2-4(18)5(3-17)21-6/h4-6,17-18H,2-3H2,1H3,(H3,12,14,15,19)/t4-,5+,6+/m0/s1

Standard InChI Key:  WNQRNUKAULNFLF-KVQBGUIXSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.7061   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215   -0.7155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7061   -1.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366   -1.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215   -2.0503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -0.5579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666    0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -2.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351   -1.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515    0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666    1.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -3.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116   -1.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8496   -0.5579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145    1.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215    2.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3695    2.8018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1991   -2.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  2  0
  7  2  1  1
  8  3  2  0
  9 10  2  0
 10  6  1  0
 11  7  1  0
 12  7  1  0
 13 11  1  0
 14 12  1  0
 15  8  1  0
 16  4  1  0
 17 10  1  0
 14 18  1  6
 13 19  1  1
 20 19  1  0
 21 16  1  0
  5  4  2  0
  9  8  1  0
 14 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3143095

   ---

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: 297.27

Molecular Weight (Monoisotopic): 297.1073

AlogP: -1.24

#Rotatable Bonds: 3

Polar Surface Area: 148.77

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.38

CX Basic pKa: ┄

CX LogP: -0.29

CX LogD: -0.29

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: 0.69

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