5-(2-Bromo-vinyl)-1-[4-hydroxy-5-(8-methyl-2-oxo-4H-2lambda*5*-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

ID: ALA2368140

Chembl Id: CHEMBL2368140

PubChem CID: 6478055

Max Phase: Preclinical

Molecular Formula: C19H20BrN2O8P

Molecular Weight: 515.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1OP(=O)(OC[C@H]1O[C@@H](n3cc(/C=C/Br)c(=O)[nH]c3=O)C[C@@H]1O)OC2

Standard InChI:  InChI=1S/C19H20BrN2O8P/c1-11-3-2-4-13-9-27-31(26,30-17(11)13)28-10-15-14(23)7-16(29-15)22-8-12(5-6-20)18(24)21-19(22)25/h2-6,8,14-16,23H,7,9-10H2,1H3,(H,21,24,25)/b6-5+/t14-,15+,16+,31?/m0/s1

Standard InChI Key:  NHJYARJSYQQDFV-ZRCZOWOTSA-N

Alternative Forms

1. Parent:

   

   ALA2368140

   5-[(E)-2-bromovinyl]-1-[(2R,4S,5R)-4-hydroxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]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: 515.25

Molecular Weight (Monoisotopic): 514.0141

AlogP: 2.59

#Rotatable Bonds: 5

Polar Surface Area: 129.08

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: 0.52

References

1. Meier C, Lomp A, Meerbach A, Wutzler P..  (2002)  CycloSal-BVDUMP pronucleotides: how to convert an antiviral-inactive nucleoside analogue into a bioactive compound against EBV.,  45  (23): [PMID:12408726] [10.1021/jm0209275]

2. Randhawa P, Zemlicka J, Sauerbrei A, Meier C, Hostetler KY, Beadle JR, Farasati NA, Huang Y, Bradley M..  (2008)  Anti-BK virus activity of nucleoside analogs.,  52  (4): [PMID:18285481] [10.1128/aac.01241-07]

Source

Source(1):

• Scientific Literature