[4-(6-Amino-purin-9-yloxy)-but-1-enyl]-phosphonic acid

ID: ALA27301

Chembl Id: CHEMBL27301

PubChem CID: 6474323

Max Phase: Preclinical

Molecular Formula: C9H12N5O4P

Molecular Weight: 285.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2OCC/C=C/P(=O)(O)O

Standard InChI:  InChI=1S/C9H12N5O4P/c10-8-7-9(12-5-11-8)14(6-13-7)18-3-1-2-4-19(15,16)17/h2,4-6H,1,3H2,(H2,10,11,12)(H2,15,16,17)/b4-2+

Standard InChI Key:  NDUZBIYAVVGZQH-DUXPYHPUSA-N

Alternative Forms

1. Parent:

   

   ALA27301

   [(E)-4-(6-aminopurin-9-yl)oxybut-1-enyl]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: 285.20

Molecular Weight (Monoisotopic): 285.0627

AlogP: -0.08

#Rotatable Bonds: 5

Polar Surface Area: 136.38

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: 1.54

CX LogP: -1.39

CX LogD: -3.71

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.51

Np Likeness Score: 0.38

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. 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