[2-(6-Amino-purin-9-yloxy)-ethoxymethyl]-phosphonic acid (BRL 47923)

ID: ALA285316

Chembl Id: CHEMBL285316

Cas Number: 124076-74-0

PubChem CID: 473139

Max Phase: Preclinical

Molecular Formula: C8H12N5O5P

Molecular Weight: 289.19

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BRL-47923 | BRL 47923|BRL-47923|9-(2-(Phosphonomethoxy)ethoxy)adenine|124076-74-0|9-[2-(Phosphonomethoxy)ethoxy]adenine|2-(6-aminopurin-9-yl)oxyethoxymethylphosphonic acid|CHEMBL285316|SCHEMBL2107417|DTXSID20154216|HRVFEVBDZIXIGY-UHFFFAOYSA-N

Canonical SMILES:  Nc1ncnc2c1ncn2OCCOCP(=O)(O)O

Standard InChI:  InChI=1S/C8H12N5O5P/c9-7-6-8(11-3-10-7)13(4-12-6)18-2-1-17-5-19(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)

Standard InChI Key:  HRVFEVBDZIXIGY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA285316

   9-(2-(Phosphonomethoxy)ethoxy)adenine

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: 289.19

Molecular Weight (Monoisotopic): 289.0576

AlogP: -1.01

#Rotatable Bonds: 6

Polar Surface Area: 145.61

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: 1.76

CX LogP: -2.67

CX LogD: -4.29

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.45

Np Likeness Score: -0.16

References

1. Harnden MR, Parkin A, Parratt MJ, Perkins RM..  (1993)  Novel acyclonucleotides: synthesis and antiviral activity of alkenylphosphonic acid derivatives of purines and a pyrimidine.,  36  (10): [PMID:8496903] [10.1021/jm00062a006]

2. Serafinowska HT, Ashton RJ, Bailey S, Harnden MR, Jackson SM, Sutton D..  (1995)  Synthesis and in vivo evaluation of prodrugs of 9-[2-(phosphonomethoxy)ethoxy]adenine.,  38  (8): [PMID:7731022] [10.1021/jm00008a015]

3. Harnden MR, Jarvest RL.  (1992)  Synthesis of 9-[2-(phosphonomethoxy)ethylamino]adenine and 9-[(phosphonomethoxy)acetamido]adenine, analogues of a potent anti-HIV acyclonucleotide,  2  (12): [10.1016/S0960-894X(00)80428-X]

Source

Source(1):

• Scientific Literature