((2S,3R,4S,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methyltriphosphoric acid

ID: ALA4592496

Chembl Id: CHEMBL4592496

PubChem CID: 155569058

Max Phase: Preclinical

Molecular Formula: C9H12ClF2N2O14P3

Molecular Weight: 538.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1ccn([C@@H]2O[C@](F)(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/C9H12ClF2N2O14P3/c10-9(12)5(16)8(11,26-6(9)14-2-1-4(15)13-7(14)17)3-25-30(21,22)28-31(23,24)27-29(18,19)20/h1-2,5-6,16H,3H2,(H,21,22)(H,23,24)(H,13,15,17)(H2,18,19,20)/t5-,6-,8-,9-/m1/s1

Standard InChI Key:  JSZRWPLFOYFPBV-SQEXRHODSA-N

Alternative Forms

1. Parent:

   

   ALA4592496

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 538.57

Molecular Weight (Monoisotopic): 537.9158

AlogP: -0.66

#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: 0.89

CX Basic pKa: ┄

CX LogP: -1.05

CX LogD: -8.46

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.18

Np Likeness Score: 0.80

References

1. 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