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

ID: ALA1652466

Chembl Id: CHEMBL1652466

PubChem CID: 136030640

Max Phase: Preclinical

Molecular Formula: C8H13N5O8P2

Molecular Weight: 369.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H13N5O8P2/c9-8-11-6-5(7(14)12-8)10-3-13(6)1-2-20-4-22(15,16)21-23(17,18)19/h3H,1-2,4H2,(H,15,16)(H2,17,18,19)(H3,9,11,12,14)

Standard InChI Key:  HTCVLHBMFDJHHS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1652466

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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: 369.17

Molecular Weight (Monoisotopic): 369.0239

AlogP: -1.03

#Rotatable Bonds: 7

Polar Surface Area: 202.88

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.70

CX Basic pKa: 3.27

CX LogP: -2.35

CX LogD: -6.50

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: -0.16

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