({[({[2-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)ethoxy]methyl}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

ID: ALA1652467

Chembl Id: CHEMBL1652467

PubChem CID: 135485600

Max Phase: Preclinical

Molecular Formula: C8H14N5O11P3

Molecular Weight: 449.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)c2ncn(CCOCP(=O)(O)OP(=O)(O)OP(=O)(O)O)c2[nH]1

Standard InChI:  InChI=1S/C8H14N5O11P3/c9-8-11-6-5(7(14)12-8)10-3-13(6)1-2-22-4-25(15,16)23-27(20,21)24-26(17,18)19/h3H,1-2,4H2,(H,15,16)(H,20,21)(H2,17,18,19)(H3,9,11,12,14)

Standard InChI Key:  WIQKIFHQKGWZBQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1652467

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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

Calculated Properties

Molecular Weight: 449.15

Molecular Weight (Monoisotopic): 448.9903

AlogP: -0.91

#Rotatable Bonds: 9

Polar Surface Area: 249.41

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.71

CX Basic pKa: 2.21

CX LogP: -2.73

CX LogD: -9.12

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.20

Np Likeness Score: 0.07

References

1. Wolfgang GH, Shibata R, Wang J, Ray AS, Wu S, Doerrfler E, Reiser H, Lee WA, Birkus G, Christensen ND, Andrei G, Snoeck R..  (2009)  GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions.,  53  (7): [PMID:19398642] [10.1128/aac.00103-09]

Source

Source(1):

• Scientific Literature