Isopropyl ((S)-(((2R,3R,4R,5R)-5-(3-pentyloxyformyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4533537

PubChem CID: 155547460

Max Phase: Preclinical

Molecular Formula: C28H39FN3O11P

Molecular Weight: 643.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCOC(=O)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/C28H39FN3O11P/c1-6-7-11-16-39-27(37)32-22(33)14-15-31(26(32)36)25-28(5,29)23(34)21(42-25)17-40-44(38,43-20-12-9-8-10-13-20)30-19(4)24(35)41-18(2)3/h8-10,12-15,18-19,21,23,25,34H,6-7,11,16-17H2,1-5H3,(H,30,38)/t19-,21+,23+,25+,28+,44-/m0/s1

Standard InChI Key:  DAEYNRYGQZBPHQ-OEDGJYFXSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4533537

   ---

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: 643.60

Molecular Weight (Monoisotopic): 643.2306

AlogP: 3.30

#Rotatable Bonds: 14

Polar Surface Area: 173.62

Molecular Species: NEUTRAL

HBA: 13

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.17

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