1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-thiophen-2-yl-1H-pyrimidine-2,4-dione

ID: ALA610367

PubChem CID: 46875498

Max Phase: Preclinical

Molecular Formula: C13H14N2O6S

Molecular Weight: 326.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n(C2O[C@H](CO)[C@@H](O)[C@@H]2O)cc1-c1cccs1

Standard InChI:  InChI=1S/C13H14N2O6S/c16-5-7-9(17)10(18)12(21-7)15-4-6(8-2-1-3-22-8)11(19)14-13(15)20/h1-4,7,9-10,12,16-18H,5H2,(H,14,19,20)/t7-,9-,10+,12?/m1/s1

Standard InChI Key:  DCIPFACYLTURBG-HUABOAPESA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.8875   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -1.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -4.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -1.6292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -2.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -6.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -6.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -4.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  2  0
  5  3  1  0
  6  1  1  0
  7  4  1  0
  8  2  1  0
  9  2  1  0
 10  8  1  0
 11  9  1  0
 12  4  1  0
 13 12  1  0
 14  3  2  0
 15  7  2  0
 16 12  2  0
 17 13  1  0
 18 16  1  0
  8 19  1  1
 10 20  1  6
 11 21  1  1
 22 21  1  0
  7  5  1  0
 10 11  1  0
 18 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA610367

   1-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-thiophen-2-ylpyrimidine-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: 326.33

Molecular Weight (Monoisotopic): 326.0573

AlogP: -1.12

#Rotatable Bonds: 3

Polar Surface Area: 124.78

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.54

CX Basic pKa: ┄

CX LogP: -0.83

CX LogD: -0.84

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 0.30

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