4-Amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-thiophen-2-yl-1H-pyrimidin-2-one

ID: ALA2367581

Cas Number: 134333-67-8

PubChem CID: 512325

Max Phase: Preclinical

Molecular Formula: C13H15N3O4S

Molecular Weight: 309.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1-c1cccs1

Standard InChI:  InChI=1S/C13H15N3O4S/c14-12-7(10-2-1-3-21-10)5-16(13(19)15-12)11-4-8(18)9(6-17)20-11/h1-3,5,8-9,11,17-18H,4,6H2,(H2,14,15,19)/t8-,9+,11+/m0/s1

Standard InChI Key:  XGDYHDVQDBZPGC-IQJOONFLSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  1  0  0  0  0  0999 V2000
    3.6542   -2.2096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596   -2.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747   -2.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8035   -3.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6240   -3.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -2.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4242   -0.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680   -4.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568   -0.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -0.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610   -4.5560    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102   -1.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8805   -5.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748   -5.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1089   -4.2120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -5.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -0.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    0.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  7  2  0
  5  1  1  1
  6  4  1  0
  7  1  1  0
  8  5  1  0
  5  9  1  0
 10  4  1  0
 11  8  1  0
 12  9  1  0
 13 10  1  0
 14  3  2  0
 15 10  2  0
 16 13  1  0
 17  6  1  0
 18 15  1  0
 12 19  1  6
 11 20  1  1
 21 20  1  0
  6  2  2  0
 11 12  1  0
 18 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2367581

   4-Amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-thiophen-2-yl-1H-pyrimidin-2-one

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: 309.35

Molecular Weight (Monoisotopic): 309.0783

AlogP: 0.19

#Rotatable Bonds: 3

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: ┄

CX LogP: -0.32

CX LogD: -0.32

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.75

Np Likeness Score: 0.20

References

1. 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