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

ID: ALA2368950

Cas Number: 133040-37-6

PubChem CID: 5271261

Max Phase: Preclinical

Molecular Formula: C18H17N3O5S

Molecular Weight: 387.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1-c1nc(-c2ccccc2)cs1

Standard InChI:  InChI=1S/C18H17N3O5S/c22-8-14-13(23)6-15(26-14)21-7-11(16(24)20-18(21)25)17-19-12(9-27-17)10-4-2-1-3-5-10/h1-5,7,9,13-15,22-23H,6,8H2,(H,20,24,25)/t13-,14+,15+/m0/s1

Standard InChI Key:  JYGFEAAJLLVCDX-RRFJBIMHSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    2.4202   -0.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    1.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407    0.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.7583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    2.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847   -0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913    1.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353    0.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    2.7915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777   -1.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3734    3.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    2.0069    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060    2.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915   -1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9451   -2.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7256   -0.6628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    2.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3734    4.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -2.9699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -2.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -3.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    4.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    4.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    5.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    5.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3734    5.7515    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  2  1  0
  6  1  1  1
  7  2  1  0
  8  1  1  0
  9  5  2  0
 10  6  1  0
 11  9  1  0
 12  5  1  0
  6 13  1  0
 14 12  1  0
 15 10  1  0
 16 13  1  0
 17  3  2  0
 18  7  2  0
 19 11  1  0
 16 20  1  6
 15 21  1  1
 22 21  1  0
 23 19  2  0
 24 19  1  0
 25 24  2  0
 26 23  1  0
 27 25  1  0
  4  7  1  0
 15 16  1  0
 11 14  2  0
 27 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368950

   1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(4-phenyl-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: 387.42

Molecular Weight (Monoisotopic): 387.0889

AlogP: 0.97

#Rotatable Bonds: 4

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: 1.22

CX LogD: 1.22

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.17

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