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

ID: ALA1652469

Chembl Id: CHEMBL1652469

PubChem CID: 53324652

Max Phase: Preclinical

Molecular Formula: C11H19N6O10P3

Molecular Weight: 488.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(NC2CC2)c2ncn(CCOCP(=O)(O)OP(=O)(O)OP(=O)(O)O)c2n1

Standard InChI:  InChI=1S/C11H19N6O10P3/c12-11-15-9(14-7-1-2-7)8-10(16-11)17(5-13-8)3-4-25-6-28(18,19)26-30(23,24)27-29(20,21)22/h5,7H,1-4,6H2,(H,18,19)(H,23,24)(H2,20,21,22)(H3,12,14,15,16)

Standard InChI Key:  PPJGRINGMNIPRG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1652469

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

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: 488.23

Molecular Weight (Monoisotopic): 488.0376

AlogP: 0.37

#Rotatable Bonds: 11

Polar Surface Area: 241.47

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -5.44

CX Basic pKa: 6.32

CX LogP: -3.79

CX LogD: -8.59

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.18

Np Likeness Score: -0.32

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