((2R,3R,4R,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxy-4-methyltetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate

ID: ALA4069349

Chembl Id: CHEMBL4069349

PubChem CID: 73669532

Max Phase: Unknown

Molecular Formula: C10H16ClN2O14P3

Molecular Weight: 516.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4a-tp | CHEMBL4069349|SCHEMBL16480833|BDBM50261285

Canonical SMILES:  C[C@@]1(Cl)[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O[C@H]1n1ccc(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H16ClN2O14P3/c1-10(11)7(15)5(25-8(10)13-3-2-6(14)12-9(13)16)4-24-29(20,21)27-30(22,23)26-28(17,18)19/h2-3,5,7-8,15H,4H2,1H3,(H,20,21)(H,22,23)(H,12,14,16)(H2,17,18,19)/t5-,7-,8-,10-/m1/s1

Standard InChI Key:  CQGVBTRRZXYUGC-VPCXQMTMSA-N

Alternative Forms

1. Parent:

   

   ALA4069349

   4A-TP

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: 516.61

Molecular Weight (Monoisotopic): 515.9503

AlogP: -0.86

#Rotatable Bonds: 8

Polar Surface Area: 244.14

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.90

CX Basic pKa: ┄

CX LogP: -1.75

CX LogD: -9.16

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.18

Np Likeness Score: 1.20

References

1. Alexandre FR, Badaroux E, Bilello JP, Bot S, Bouisset T, Brandt G, Cappelle S, Chapron C, Chaves D, Convard T, Counor C, Da Costa D, Dukhan D, Gay M, Gosselin G, Griffon JF, Gupta K, Hernandez-Santiago B, La Colla M, Lioure MP, Milhau J, Paparin JL, Peyronnet J, Parsy C, Pierra Rouvière C, Rahali H, Rahali R, Salanson A, Seifer M, Serra I, Standring D, Surleraux D, Dousson CB..  (2017)  The discovery of IDX21437: Design, synthesis and antiviral evaluation of 2'-α-chloro-2'-β-C-methyl branched uridine pronucleotides as potent liver-targeted HCV polymerase inhibitors.,  27  (18): [PMID:28835346] [10.1016/j.bmcl.2017.08.029]

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