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

ID: ALA3246760

PubChem CID: 135686065

Max Phase: Preclinical

Molecular Formula: C11H16N6O5

Molecular Weight: 312.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc2c(=O)[nH]c(N)nc2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H16N6O5/c1-13-11-14-4-7(15-10(12)16-8(4)21)17(11)9-6(20)5(19)3(2-18)22-9/h3,5-6,9,18-20H,2H2,1H3,(H,13,14)(H3,12,15,16,21)/t3-,5-,6-,9-/m1/s1

Standard InChI Key:  XKILAGHGKVXARL-UUOKFMHZSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.5122  -19.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925  -18.9086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403  -18.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951  -20.1677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381  -19.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1760  -18.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283  -18.0891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800  -19.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3711  -20.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665  -18.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8816  -19.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811  -20.0041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350  -18.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508  -21.3200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1846  -19.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729  -19.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257  -20.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9482  -18.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761  -20.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698  -18.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6728  -17.3813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089  -17.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  2  1  1
  2  6  1  0
  3  7  1  0
  3  8  1  0
  4  9  2  0
  5 10  1  0
 11  5  1  0
  8 12  1  0
  8 13  2  0
  9 14  1  0
 10 15  1  0
 11 16  1  0
 11 17  1  6
 15 18  1  1
 16 19  1  6
 18 20  1  0
  6  7  2  0
  9 12  1  0
 16 15  1  0
  6 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246760

   ---

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: 312.29

Molecular Weight (Monoisotopic): 312.1182

AlogP: -2.64

#Rotatable Bonds: 3

Polar Surface Area: 171.54

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.16

CX Basic pKa: 1.39

CX LogP: -2.55

CX LogD: -2.55

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.35

Np Likeness Score: 0.81

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. Jordan F, Wu A..  (1978)  Stereoelectronic factors in the binding of substrate analogues and inhibitors to purine nucleoside phosphorylase isolated from human erythrocytes.,  21  (9): [PMID:31484] [10.1021/jm00207a008]

3. Institute for Molecular Medicine Finland - High Throughput Biomedicine Unit.  (2023)  ECBD screening data for assay EOS300108,  [10.6019/EOS300108]

Source

Source(2):

• Scientific Literature
• EU-OPENSCREEN dataset