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

ID: ALA1652468

Chembl Id: CHEMBL1652468

PubChem CID: 53320320

Max Phase: Preclinical

Molecular Formula: C11H18N6O7P2

Molecular Weight: 408.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H18N6O7P2/c12-11-15-9(14-7-1-2-7)8-10(16-11)17(5-13-8)3-4-23-6-25(18,19)24-26(20,21)22/h5,7H,1-4,6H2,(H,18,19)(H2,20,21,22)(H3,12,14,15,16)

Standard InChI Key:  RAGKALDUAYWVMO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1652468

   {[({2-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]ethoxy}methyl)(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: 408.25

Molecular Weight (Monoisotopic): 408.0712

AlogP: 0.25

#Rotatable Bonds: 9

Polar Surface Area: 194.94

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.65

CX Basic pKa: 6.35

CX LogP: -3.71

CX LogD: -5.97

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: -0.59

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