(S)-2,6-Diamino-N6-(N,N-dimethylaminoethyl)-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine

ID: ALA1766201

Chembl Id: CHEMBL1766201

PubChem CID: 54583438

Max Phase: Preclinical

Molecular Formula: C13H23FN7O4P

Molecular Weight: 391.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H23FN7O4P/c1-20(2)4-3-16-11-10-12(19-13(15)18-11)21(7-17-10)6-9(5-14)25-8-26(22,23)24/h7,9H,3-6,8H2,1-2H3,(H2,22,23,24)(H3,15,16,18,19)/t9-/m1/s1

Standard InChI Key:  HPOFADNDLPZZGI-SECBINFHSA-N

Alternative Forms

1. Parent:

   

   ALA1766201

   [(2S)-1-[2-amino-6-[2-(dimethylamino)ethylamino]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: 391.34

Molecular Weight (Monoisotopic): 391.1533

AlogP: -0.13

#Rotatable Bonds: 10

Polar Surface Area: 151.65

Molecular Species: ZWITTERION

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.35

CX Basic pKa: 8.72

CX LogP: -2.63

CX LogD: -2.75

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -0.80

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