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

ID: ALA4536594

PubChem CID: 155548751

Max Phase: Preclinical

Molecular Formula: C23H31FN3O9P

Molecular Weight: 543.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccn([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)c(=O)n1

Standard InChI:  InChI=1S/C23H31FN3O9P/c1-14(2)34-20(29)15(3)26-37(31,36-16-9-7-6-8-10-16)33-13-17-19(28)23(4,24)21(35-17)27-12-11-18(32-5)25-22(27)30/h6-12,14-15,17,19,21,28H,13H2,1-5H3,(H,26,31)/t15-,17+,19+,21+,23+,37-/m0/s1

Standard InChI Key:  TXHFSJCQLSGTRF-HEFSGLBYSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4536594

   ---

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: 543.49

Molecular Weight (Monoisotopic): 543.1782

AlogP: 2.37

#Rotatable Bonds: 11

Polar Surface Area: 147.44

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 1.76

CX LogD: 1.76

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.32

Np Likeness Score: 0.14

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