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

ID: ALA2368955

Cas Number: 133040-38-7

PubChem CID: 5271262

Max Phase: Preclinical

Molecular Formula: C13H15N3O5S

Molecular Weight: 325.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1csc(-c2cn([C@H]3C[C@H](O)[C@@H](CO)O3)c(=O)[nH]c2=O)n1

Standard InChI:  InChI=1S/C13H15N3O5S/c1-6-5-22-12(14-6)7-3-16(13(20)15-11(7)19)10-2-8(18)9(4-17)21-10/h3,5,8-10,17-18H,2,4H2,1H3,(H,15,19,20)/t8-,9+,10+/m0/s1

Standard InChI Key:  UEVROUDNJQKVJJ-IVZWLZJFSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    4.7864   -3.1945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918   -3.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4508   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9358   -4.6156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3015   -2.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9123   -3.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7562   -4.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6069   -3.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643   -4.3026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -1.7424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765   -2.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3248   -2.9750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -1.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2180   -3.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215   -1.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1318   -3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6304   -4.0344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2412   -5.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369   -1.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -0.0200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9325   -4.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  2  0
  3  1  1  0
  4  3  1  0
  5  1  1  1
  6  2  1  0
  7  2  1  0
  8  1  1  0
  9  6  2  0
 10  5  1  0
  5 11  1  0
 12  6  1  0
 13 10  1  0
 14  9  1  0
 15 11  1  0
 16 12  1  0
 17  3  2  0
 18  7  2  0
 15 19  1  6
 13 20  1  1
 21 20  1  0
 22 14  1  0
  4  7  1  0
 13 15  1  0
 14 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368955

   1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(4-methyl-thiazol-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: 325.35

Molecular Weight (Monoisotopic): 325.0732

AlogP: -0.39

#Rotatable Bonds: 3

Polar Surface Area: 117.44

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.48

CX Basic pKa: ┄

CX LogP: -0.68

CX LogD: -0.68

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: -0.09

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