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

ID: ALA2021338

Cas Number: 127235-63-6

PubChem CID: 512328

Max Phase: Preclinical

Molecular Formula: C13H14N2O5S

Molecular Weight: 310.33

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-c1cccs1

Standard InChI:  InChI=1S/C13H14N2O5S/c16-6-9-8(17)4-11(20-9)15-5-7(10-2-1-3-21-10)12(18)14-13(15)19/h1-3,5,8-9,11,16-17H,4,6H2,(H,14,18,19)/t8-,9+,11-/m0/s1

Standard InChI Key:  PCDQBRGMSMVLDZ-NGZCFLSTSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  1  0  0  0  0  0999 V2000
    6.9490   -2.6261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6584   -2.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6459   -3.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3636   -2.6303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1524   -2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3636   -3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9448   -3.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945   -1.8959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -3.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6459   -4.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0449   -2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432   -3.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8245   -4.6796    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6584   -1.3981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0730   -3.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0566   -5.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4138   -5.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8328   -6.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076   -3.9246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650   -2.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032   -1.3359    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  6
  6  3  1  0
  7  1  1  0
  8  5  1  0
  5  9  1  0
 10  3  1  0
 11  8  1  0
 12  9  1  0
 13 10  1  0
 14  2  2  0
 15  6  2  0
 16 10  2  0
 17 13  1  0
 18 16  1  0
 12 19  1  6
 11 20  1  1
 21 20  1  0
  6  4  1  0
 11 12  1  0
 17 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2021338

   1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-thiophen-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: 310.33

Molecular Weight (Monoisotopic): 310.0623

AlogP: -0.09

#Rotatable Bonds: 3

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.54

CX Basic pKa: ┄

CX LogP: 0.07

CX LogD: 0.06

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 0.10

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