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

ID: ALA4088430

Chembl Id: CHEMBL4088430

PubChem CID: 117940941

Max Phase: Preclinical

Molecular Formula: C9H13ClFN2O14P3

Molecular Weight: 520.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@]2(F)Cl)c(=O)[nH]1

Standard InChI:  InChI=1S/C9H13ClFN2O14P3/c10-9(11)6(15)4(25-7(9)13-2-1-5(14)12-8(13)16)3-24-29(20,21)27-30(22,23)26-28(17,18)19/h1-2,4,6-7,15H,3H2,(H,20,21)(H,22,23)(H,12,14,16)(H2,17,18,19)/t4-,6-,7-,9-/m1/s1

Standard InChI Key:  RHZJHRBEIVLNRD-FJGDRVTGSA-N

Alternative Forms

1. Parent:

   

   ALA4088430

   [[(2R,3R,4S,5R)-4-chloro-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate

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: 520.58

Molecular Weight (Monoisotopic): 519.9252

AlogP: -0.96

#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: -1.62

CX LogD: -9.03

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.18

Np Likeness Score: 1.04

References

1. Zhou S, Mahmoud S, Liu P, Zhou L, Ehteshami M, Bassit L, Tao S, Domaoal RA, Sari O, Schutter C, Amiralaei S, Khalil A, Ollinger Russell O, McBrayer T, Whitaker T, Abou-Taleb N, Amblard F, Coats SJ, Schinazi RF..  (2017)  2'-Chloro,2'-fluoro Ribonucleotide Prodrugs with Potent Pan-genotypic Activity against Hepatitis C Virus Replication in Culture.,  60  (13): [PMID:28595015] [10.1021/acs.jmedchem.7b00067]

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]

Source

Source(1):

• Scientific Literature