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

ID: ALA2368956

Cas Number: 133040-36-5

PubChem CID: 512320

Max Phase: Preclinical

Molecular Formula: C12H13N3O5S

Molecular Weight: 311.32

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-c1nccs1

Standard InChI:  InChI=1S/C12H13N3O5S/c16-5-8-7(17)3-9(20-8)15-4-6(10(18)14-12(15)19)11-13-1-2-21-11/h1-2,4,7-9,16-17H,3,5H2,(H,14,18,19)/t7-,8+,9+/m0/s1

Standard InChI Key:  CJYNUNQROFDZQF-DJLDLDEBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  1  0  0  0  0  0999 V2000
   -0.1912   -4.7737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -5.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142   -5.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -6.1948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -4.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787   -6.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293   -4.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9347   -5.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4212   -3.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -4.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867   -5.8817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886   -2.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560   -3.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472   -4.5542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3472   -5.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2636   -6.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2404   -5.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -4.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -3.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886   -2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031   -1.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  2  0
  4  2  1  0
  5  1  1  1
  6  3  1  0
  7  1  1  0
  8  3  1  0
  9  5  1  0
  5 10  1  0
 11  8  2  0
 12  9  1  0
 13 10  1  0
 14  8  1  0
 15  2  2  0
 16  6  2  0
 17 11  1  0
 18 14  1  0
 13 19  1  6
 12 20  1  1
 21 20  1  0
  4  6  1  0
 12 13  1  0
 17 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368956

   1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-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: 311.32

Molecular Weight (Monoisotopic): 311.0576

AlogP: -0.70

#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: -0.81

CX LogD: -0.81

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 0.13

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]

2. Wigerinck P, Pannecouque C, Snoeck R, Claes P, De Clercq E, Herdewijn P..  (1991)  5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication.,  34  (8): [PMID:1652017] [10.1021/jm00112a011]

Source

Source(1):

• Scientific Literature