Isopropyl ((S)-(((2R,3R,4R,5R)-5-(3-(1-((isopropoxycarbonyl)oxy)ethyl)-2,4-dioxo-3,4-di-hydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4474563

PubChem CID: 155537298

Max Phase: Preclinical

Molecular Formula: C28H39FN3O12P

Molecular Weight: 659.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)OC(C)n1c(=O)ccn([C@@H]2O[C@H](CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)Oc3ccccc3)[C@@H](O)[C@@]2(C)F)c1=O

Standard InChI:  InChI=1S/C28H39FN3O12P/c1-16(2)40-24(35)18(5)30-45(38,44-20-11-9-8-10-12-20)39-15-21-23(34)28(7,29)25(43-21)31-14-13-22(33)32(26(31)36)19(6)42-27(37)41-17(3)4/h8-14,16-19,21,23,25,34H,15H2,1-7H3,(H,30,38)/t18-,19?,21+,23+,25+,28+,45-/m0/s1

Standard InChI Key:  ZHLNYVVCYYEXAG-CTXLNMGFSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4474563

   ---

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: 659.60

Molecular Weight (Monoisotopic): 659.2255

AlogP: 3.21

#Rotatable Bonds: 13

Polar Surface Area: 182.85

Molecular Species: NEUTRAL

HBA: 14

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.24

Np Likeness Score: 0.15

References

1. Guo S, Xu M, Guo Q, Zhu F, Jiang X, Xie Y, Shen J..  (2019)  Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents.,  27  (5): [PMID:30683552] [10.1016/j.bmc.2019.01.007]

Source

Source(1):

• Scientific Literature