5-(3-Ethyl-isoxazol-5-yl)-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA2368959

Cas Number: 133040-33-2

PubChem CID: 5271260

Max Phase: Preclinical

Molecular Formula: C14H17N3O6

Molecular Weight: 323.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(-c2cn([C@H]3C[C@H](O)[C@@H](CO)O3)c(=O)[nH]c2=O)on1

Standard InChI:  InChI=1S/C14H17N3O6/c1-2-7-3-10(23-16-7)8-5-17(14(21)15-13(8)20)12-4-9(19)11(6-18)22-12/h3,5,9,11-12,18-19H,2,4,6H2,1H3,(H,15,20,21)/t9-,11+,12+/m0/s1

Standard InChI Key:  VQSOWKCELBIFTO-MVWJERBFSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  1  0  0  0  0  0999 V2000
    2.8666   -2.7650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720   -3.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311   -3.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0160   -4.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817   -2.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8365   -4.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871   -2.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -3.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -1.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -2.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5446   -3.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050   -2.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -3.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -0.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2120   -2.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -3.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214   -4.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5172   -1.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547    0.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251   -2.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536   -1.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  2  0
  3  1  1  0
  4  3  1  0
  5  1  1  1
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  5  1  0
  5 10  1  0
 11  8  1  0
 12  8  2  0
 13 11  1  0
 14  9  1  0
 15 10  1  0
 16 12  1  0
 17  3  2  0
 18  6  2  0
 15 19  1  6
 14 20  1  1
 21 20  1  0
 22 16  1  0
 23 22  1  0
  4  6  1  0
 14 15  1  0
 13 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368959

   5-(3-Ethyl-isoxazol-5-yl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H--pyrimidine-2,4-dione

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: 323.31

Molecular Weight (Monoisotopic): 323.1117

AlogP: -0.61

#Rotatable Bonds: 4

Polar Surface Area: 130.58

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.49

CX Basic pKa: 0.44

CX LogP: -0.73

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.08

References

1. Wigerinck P, Snoeck R, Claes P, De Clercq E, Herdewijn P..  (1991)  Synthesis and antiviral activity of 5-heteroaryl-substituted 2'-deoxyuridines.,  34  (6): [PMID:2061920] [10.1021/jm00110a003]

Source

Source(1):

• Scientific Literature