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

ID: ALA2112150

Cas Number: 479681-73-7

PubChem CID: 6478667

Max Phase: Preclinical

Molecular Formula: C11H13BrN2O4

Molecular Weight: 317.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2CO[C@H](CO)C2)cc1/C=C/Br

Standard InChI:  InChI=1S/C11H13BrN2O4/c12-2-1-7-4-14(11(17)13-10(7)16)8-3-9(5-15)18-6-8/h1-2,4,8-9,15H,3,5-6H2,(H,13,16,17)/b2-1+/t8-,9-/m0/s1

Standard InChI Key:  PUVOYSWPIMMHQU-XOINZRLQSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  1  0  0  0  0  0999 V2000
    2.4050   -1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050   -0.4050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190   -1.6534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371   -0.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371   -1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0856   -3.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714   -3.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5511    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6827   -1.6451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7098   -2.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1106    0.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574   -2.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651   -0.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330   -2.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9791    0.0208    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -2.7850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -2.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  2  0
  5  3  1  0
  6  2  1  0
  8  7  1  0
  9  4  1  0
 10  1  2  0
 11 13  1  0
 12  6  2  0
  7 13  1  0
 14  9  2  0
 15  8  1  0
 16 14  1  0
 17 18  1  0
 15 18  1  1
  6  4  1  0
 15 11  1  0
  7  3  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2112150

   BVisoDDU

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: 317.14

Molecular Weight (Monoisotopic): 316.0059

AlogP: 0.22

#Rotatable Bonds: 3

Polar Surface Area: 84.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.79

CX Basic pKa: ┄

CX LogP: -0.34

CX LogD: -0.34

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.84

Np Likeness Score: 0.45

References

1. Guenther S, Balzarini J, De Clercq E, Nair V..  (2002)  A thymidine phosphorylase-stable analogue of BVDU with significant antiviral activity.,  45  (25): [PMID:12459010] [10.1021/jm025569k]

Source

Source(1):

• Scientific Literature