ID: ALA4455349

Max Phase: Preclinical

Molecular Formula: C21H26BrFN3O9P

Molecular Weight: 594.33

Molecule Type: Unknown

Representations

Canonical SMILES:  CC(C)OC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@](F)(Br)[C@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C21H26BrFN3O9P/c1-12(2)33-18(29)13(3)25-36(31,35-14-7-5-4-6-8-14)32-11-15-17(28)21(22,23)19(34-15)26-10-9-16(27)24-20(26)30/h4-10,12-13,15,17,19,28H,11H2,1-3H3,(H,25,31)(H,24,27,30)/t13-,15+,17-,19+,21-,36-/m0/s1

Standard InChI Key:  ZTJBRLHJSDGEDC-JGNVGUCCSA-N

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

Properties

Molecular Weight: 594.33

Molecular Weight (Monoisotopic): 593.0574

AlogP: 1.99

#Rotatable Bonds: 10

Polar Surface Area: 158.18

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.73

CX Basic pKa:

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.21

Np Likeness Score: 0.20

References

1. Mengshetti S, Zhou L, Sari O, De Schutter C, Zhang H, Cho JH, Tao S, Bassit LC, Verma K, Domaoal RA, Ehteshami M, Jiang Y, Ovadia R, Kasthuri M, Ollinger Russell O, McBrayer T, Whitaker T, Pattassery J, Pascual ML, Uher L, Lin BY, Lee S, Amblard F, Coats SJ, Schinazi RF..  (2019)  Discovery of a Series of 2'-α-Fluoro,2'-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus.,  62  (4): [PMID:30653317] [10.1021/acs.jmedchem.8b01300]

Source

Source(1):

• Scientific Literature