[3-(2-Amino-6-oxo-1,6-dihydro-purin-9-ylmethyl)-buta-1,3-dienyl]-phosphonic acid

ID: ALA27200

Chembl Id: CHEMBL27200

PubChem CID: 135483978

Max Phase: Preclinical

Molecular Formula: C10H12N5O4P

Molecular Weight: 297.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(/C=C/P(=O)(O)O)Cn1cnc2c(O)nc(N)nc21

Standard InChI:  InChI=1S/C10H12N5O4P/c1-6(2-3-20(17,18)19)4-15-5-12-7-8(15)13-10(11)14-9(7)16/h2-3,5H,1,4H2,(H2,17,18,19)(H3,11,13,14,16)/b3-2+

Standard InChI Key:  SAQRMMZGZJVNTP-NSCUHMNNSA-N

Alternative Forms

1. Parent:

   

   ALA27200

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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: 297.21

Molecular Weight (Monoisotopic): 297.0627

AlogP: 0.36

#Rotatable Bonds: 4

Polar Surface Area: 147.38

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.53

CX Basic pKa: 1.21

CX LogP: -0.55

CX LogD: -2.87

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: -0.01

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. Nave J, Casara PJ, Taylor DL, Stanley Tyms A, Kenny M, HalazyS S.  (1996)  Synthesis, enzymatic phosphorylation and antiviral activity of acyclic dienyl phosphonate derivatives of guanine,  6  (2): [10.1016/0960-894X(95)00585-H]

Source

Source(1):

• Scientific Literature