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

ID: ALA5271779

Max Phase: Preclinical

Molecular Formula: C21H27N4O8P

Molecular Weight: 494.44

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](C)N[P@@](=O)(OCC1=C[C@@H](O)[C@H](n2ccc(N)nc2=O)O1)Oc1ccccc1

Standard InChI:  InChI=1S/C21H27N4O8P/c1-13(2)31-20(27)14(3)24-34(29,33-15-7-5-4-6-8-15)30-12-16-11-17(26)19(32-16)25-10-9-18(22)23-21(25)28/h4-11,13-14,17,19,26H,12H2,1-3H3,(H,24,29)(H2,22,23,28)/t14-,17+,19+,34+/m0/s1

Standard InChI Key:  LWNCAGWHAKUXIC-CFLCUWIBSA-N

Molfile:  

 
     RDKit          2D

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 34 33  2  0
 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5271779

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 494.44

Molecular Weight (Monoisotopic): 494.1567

AlogP: 1.73

#Rotatable Bonds: 10

Polar Surface Area: 164.23

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.23

CX Basic pKa: ┄

CX LogP: 0.32

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: 0.30

References

1. Passow KT, Caldwell HS, Ngo KA, Arnold JJ, Antczak NM, Narayanan A, Jose J, Sturla SJ, Cameron CE, Ciota AT, Harki DA..  (2021)  A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide.,  64  (20.0): [PMID:34661397] [10.1021/acs.jmedchem.1c01481]

Source

Source(1):

• Scientific Literature