(S)-2-Amino-9-[3-fluoro-2-(phosphonomethoxy)-propyl]-6-(pyrrolidin-1-yl)purine

ID: ALA1766280

Chembl Id: CHEMBL1766280

PubChem CID: 54581463

Max Phase: Preclinical

Molecular Formula: C13H20FN6O4P

Molecular Weight: 374.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CCCC2)c2ncn(C[C@@H](CF)OCP(=O)(O)O)c2n1

Standard InChI:  InChI=1S/C13H20FN6O4P/c14-5-9(24-8-25(21,22)23)6-20-7-16-10-11(19-3-1-2-4-19)17-13(15)18-12(10)20/h7,9H,1-6,8H2,(H2,15,17,18)(H2,21,22,23)/t9-/m1/s1

Standard InChI Key:  FOVANXUAPNKSDQ-SECBINFHSA-N

Alternative Forms

1. Parent:

   

   ALA1766280

   [(2S)-1-(2-amino-6-pyrrolidin-1-ylpurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic 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: 374.31

Molecular Weight (Monoisotopic): 374.1268

AlogP: 0.50

#Rotatable Bonds: 7

Polar Surface Area: 139.62

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.40

CX Basic pKa: 5.26

CX LogP: -2.98

CX LogD: -2.48

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -0.70

References

1. Baszczyňski O, Jansa P, Dračínský M, Klepetářová B, Holý A, Votruba I, de Clercq E, Balzarini J, Janeba Z..  (2011)  Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines.,  19  (7): [PMID:21429755] [10.1016/j.bmc.2011.02.050]

Source

Source(1):

• Scientific Literature