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

ID: ALA2368951

Cas Number: 133040-32-1

PubChem CID: 5271259

Max Phase: Preclinical

Molecular Formula: C13H15N3O6

Molecular Weight: 309.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cn([C@H]3C[C@H](O)[C@@H](CO)O3)c(=O)[nH]c2=O)on1

Standard InChI:  InChI=1S/C13H15N3O6/c1-6-2-9(22-15-6)7-4-16(13(20)14-12(7)19)11-3-8(18)10(5-17)21-11/h2,4,8,10-11,17-18H,3,5H2,1H3,(H,14,19,20)/t8-,10+,11+/m0/s1

Standard InChI Key:  GBLOVFDLOVVYPI-JMJZKYOTSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    2.8282   -2.7429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1336   -3.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -3.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9776   -4.1640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -2.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980   -4.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6487   -2.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9541   -3.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -1.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183   -2.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061   -3.8510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -2.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2598   -3.5154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308   -0.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2633   -1.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736   -2.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -3.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830   -4.7452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -1.0359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163    0.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7867   -2.1429    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
  4  6  1  0
 14 15  1  0
 13 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368951

   1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(3-methyl-isoxazol-5-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: 309.28

Molecular Weight (Monoisotopic): 309.0961

AlogP: -0.86

#Rotatable Bonds: 3

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: 0.56

CX LogP: -1.43

CX LogD: -1.43

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: 0.03

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