ID: ALA93006

Max Phase: Preclinical

Molecular Formula: C9H13FN5O5P

Molecular Weight: 321.20

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(O)c2ncn(C[C@H](CF)OCP(=O)(O)O)c2n1

Standard InChI:  InChI=1S/C9H13FN5O5P/c10-1-5(20-4-21(17,18)19)2-15-3-12-6-7(15)13-9(11)14-8(6)16/h3,5H,1-2,4H2,(H2,17,18,19)(H3,11,13,14,16)/t5-/m0/s1

Standard InChI Key:  KZUGHQWNFSZLLP-YFKPBYRVSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 321.20

Molecular Weight (Monoisotopic): 321.0638

AlogP: -0.40

#Rotatable Bonds: 6

Polar Surface Area: 156.61

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.35

CX Basic pKa: 0.74

CX LogP: -1.28

CX LogD: -3.32

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: -0.44

References

1. Yu KL, Bronson JJ, Yang H, Patick A, Alam M, Brankovan V, Datema R, Hitchcock MJ, Martin JC..  (1993)  Synthesis and antiviral activity of 2'-substituted 9-[2-(phosphonomethoxy)ethyl]guanine analogues.,  36  (19): [PMID:8410987] [10.1021/jm00071a003]

2. Baszczyňski O, Jansa P, Dračínský M, Klepetářová B, Holý A, Votruba I, de Clercq E, Balzarini J, Janeba Z..  (2011)  Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines.,  19  (7): [PMID:21429755] [10.1016/j.bmc.2011.02.050]

3. Baszczyňski O, Hocková D, Janeba Z, Holý A, Jansa P, Dračínský M, Keough DT, Guddat LW..  (2013)  The effect of novel [3-fluoro-(2-phosphonoethoxy)propyl]purines on the inhibition of Plasmodium falciparum, Plasmodium vivax and human hypoxanthine-guanine-(xanthine) phosphoribosyltransferases.,  67  [PMID:23850568] [10.1016/j.ejmech.2013.06.032]

4. Luo M, Groaz E, Andrei G, Snoeck R, Kalkeri R, Ptak RG, Hartman T, Buckheit RW, Schols D, De Jonghe S, Herdewijn P..  (2017)  Expanding the Antiviral Spectrum of 3-Fluoro-2-(phosphonomethoxy)propyl Acyclic Nucleoside Phosphonates: Diamyl Aspartate Amidate Prodrugs.,  60  (14): [PMID:28682067] [10.1021/acs.jmedchem.7b00416]

Source

Source(1):

• Scientific Literature