2-Hydroxymethyl-5-(6-vinyl-purin-9-yl)-tetrahydro-furan-3,4-diol

ID: ALA608036

PubChem CID: 46875850

Max Phase: Preclinical

Molecular Formula: C12H14N4O4

Molecular Weight: 278.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=Cc1ncnc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H14N4O4/c1-2-6-8-11(14-4-13-6)16(5-15-8)12-10(19)9(18)7(3-17)20-12/h2,4-5,7,9-10,12,17-19H,1,3H2/t7-,9-,10-,12?/m1/s1

Standard InChI Key:  OWIOGKLJDQSXOJ-IYYKZFDCSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.6042   -2.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -1.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -3.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -1.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -5.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -5.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -3.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  3  1  0
 12  4  1  0
 13 14  1  0
 14 11  2  0
 15 12  1  0
  6 16  1  6
  9 17  1  6
 18 15  2  0
 10 19  1  1
 20 19  1  0
  4  5  1  0
  9 10  1  0
 12 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608036

   (3R,4S,5R)-2-(6-ethenylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

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: 278.27

Molecular Weight (Monoisotopic): 278.1015

AlogP: -0.92

#Rotatable Bonds: 3

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 2.30

CX LogP: -0.89

CX LogD: -0.89

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: 1.36

References

1. Van Aerschot AA, Mamos P, Weyns NJ, Ikeda S, De Clercq E, Herdewijn PA..  (1993)  Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.,  36  (20): [PMID:8411010] [10.1021/jm00072a013]

Source

Source(1):

• Scientific Literature