(S)-(((1-((4-aminopyrimidin-2-yl)oxy)-3-fluoropropan-2-yl)oxy)methyl)phosphonic acid

ID: ALA4632934

PubChem CID: 134382682

Max Phase: Preclinical

Molecular Formula: C8H13FN3O5P

Molecular Weight: 281.18

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ccnc(OC[C@@H](CF)OCP(=O)(O)O)n1

Standard InChI:  InChI=1S/C8H13FN3O5P/c9-3-6(17-5-18(13,14)15)4-16-8-11-2-1-7(10)12-8/h1-2,6H,3-5H2,(H2,10,11,12)(H2,13,14,15)/t6-/m1/s1

Standard InChI Key:  OPVQRUQRDNDKCZ-ZCFIWIBFSA-N

Molfile:  

 
     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.6319   -3.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307   -4.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3455   -4.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620   -4.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591   -3.5963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3437   -3.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3413   -2.3621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -4.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7784   -5.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4934   -6.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4947   -6.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7809   -7.3131    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2073   -5.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9223   -6.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6362   -5.6587    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3513   -6.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6349   -4.8337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6291   -6.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4632934

   ---

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: 281.18

Molecular Weight (Monoisotopic): 281.0577

AlogP: -0.07

#Rotatable Bonds: 7

Polar Surface Area: 127.79

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: 5.84

CX LogP: -3.18

CX LogD: -3.13

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.59

Np Likeness Score: -0.13

References

1. Luo M, Groaz E, Snoeck R, Andrei G, Herdewijn P..  (2020)  Amidate Prodrugs of O-2-Alkylated Pyrimidine Acyclic Nucleosides Display Potent Anti-Herpesvirus Activity.,  11  (7): [PMID:32676147] [10.1021/acsmedchemlett.0c00090]

Source

Source(1):

• Scientific Literature