(S)-N6-Allyl-2,6-diamino-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine

ID: ALA1766199

Chembl Id: CHEMBL1766199

PubChem CID: 54581460

Max Phase: Preclinical

Molecular Formula: C12H18FN6O4P

Molecular Weight: 360.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCNc1nc(N)nc2c1ncn2C[C@@H](CF)OCP(=O)(O)O

Standard InChI:  InChI=1S/C12H18FN6O4P/c1-2-3-15-10-9-11(18-12(14)17-10)19(6-16-9)5-8(4-13)23-7-24(20,21)22/h2,6,8H,1,3-5,7H2,(H2,20,21,22)(H3,14,15,17,18)/t8-/m1/s1

Standard InChI Key:  CNCWSZLZMUZNIC-MRVPVSSYSA-N

Alternative Forms

1. Parent:

   

   ALA1766199

   [(2S)-1-[2-amino-6-(prop-2-enylamino)purin-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: 360.29

Molecular Weight (Monoisotopic): 360.1111

AlogP: 0.50

#Rotatable Bonds: 9

Polar Surface Area: 148.41

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -5.46

CX Basic pKa: 6.35

CX LogP: -3.29

CX LogD: -2.77

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.37

Np Likeness Score: -0.57

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