Isopropyl ((R)-(((2R,3R,4R,5R)-5-(3-amino-2-oxopyrazin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-D-alaninate

ID: ALA4533213

PubChem CID: 155547082

Max Phase: Preclinical

Molecular Formula: C22H31N4O9P

Molecular Weight: 526.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@@H](C)N[P@@](=O)(OC[C@H]1O[C@@H](n2ccnc(N)c2=O)[C@](C)(O)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C22H31N4O9P/c1-13(2)33-20(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-17(27)22(4,30)21(34-16)26-11-10-24-18(23)19(26)28/h5-11,13-14,16-17,21,27,30H,12H2,1-4H3,(H2,23,24)(H,25,31)/t14-,16-,17-,21-,22-,36-/m1/s1

Standard InChI Key:  UEEKKYBKWBCXFY-BKNXKGLUSA-N

Molfile:  

 
     RDKit          2D

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 21 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533213

   ---

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: 526.48

Molecular Weight (Monoisotopic): 526.1829

AlogP: 0.97

#Rotatable Bonds: 10

Polar Surface Area: 184.46

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: 5.10

CX LogP: 0.07

CX LogD: 0.07

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: 0.39

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