((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-fluoro-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate

ID: ALA4127030

Chembl Id: CHEMBL4127030

PubChem CID: 76286118

Max Phase: Unknown

Molecular Formula: C10H16FN2O15P3

Molecular Weight: 516.16

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Adafosbuvir 5'-triphosphate | CHEMBL4127030|Adafosbuvir 5'-triphosphate|SCHEMBL15833138|SCHEMBL17359506|BDBM50274118

Canonical SMILES:  C[C@]1(O)[C@H](n2ccc(=O)[nH]c2=O)O[C@](F)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@H]1O

Standard InChI:  InChI=1S/C10H16FN2O15P3/c1-9(17)6(15)10(11,26-7(9)13-3-2-5(14)12-8(13)16)4-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-3,6-7,15,17H,4H2,1H3,(H,21,22)(H,23,24)(H,12,14,16)(H2,18,19,20)/t6-,7+,9+,10+/m0/s1

Standard InChI Key:  YEFGXGBFIOVTEX-MVHNUAHISA-N

Alternative Forms

1. Parent:

   

   ALA4127030

   ADAFOSBUVIR 5'-TRIPHOSPHATE

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: 516.16

Molecular Weight (Monoisotopic): 515.9748

AlogP: -1.81

#Rotatable Bonds: 8

Polar Surface Area: 264.37

Molecular Species: ACID

HBA: 12

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.89

CX Basic pKa: ┄

CX LogP: -2.53

CX LogD: -9.94

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: 1.02

References

1. Wang G, Lim SP, Chen YL, Hunziker J, Rao R, Gu F, Seh CC, Ghafar NA, Xu H, Chan K, Lin X, Saunders OL, Fenaux M, Zhong W, Shi PY, Yokokawa F..  (2018)  Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase.,  28  (13): [PMID:29801997] [10.1016/j.bmcl.2018.04.069]

2. Wang G, Dyatkina N, Prhavc M, Williams C, Serebryany V, Hu Y, Huang Y, Wan J, Wu X, Deval J, Fung A, Jin Z, Tan H, Shaw K, Kang H, Zhang Q, Tam Y, Stoycheva A, Jekle A, Smith DB, Beigelman L..  (2019)  Synthesis and Anti-HCV Activities of 4'-Fluoro-2'-Substituted Uridine Triphosphates and Nucleotide Prodrugs: Discovery of 4'-Fluoro-2'- C-methyluridine 5'-Phosphoramidate Prodrug (AL-335) for the Treatment of Hepatitis C Infection.,  62  (9): [PMID:30951311] [10.1021/acs.jmedchem.9b00143]

3. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Active Ingredient of a Prodrug