2-(hexadecyloxy)ethyl hydrogen((S)-1-(6-amino-9H-purin-9-yl)-3-hydroxypropan-2-yloxy)methylphosphonate

ID: ALA1774183

Chembl Id: CHEMBL1774183

PubChem CID: 54582340

Max Phase: Preclinical

Molecular Formula: C27H50N5O6P

Molecular Weight: 571.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCOCCOP(=O)(O)CO[C@H](CO)Cn1cnc2c(N)ncnc21

Standard InChI:  InChI=1S/C27H50N5O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-36-17-18-38-39(34,35)23-37-24(20-33)19-32-22-31-25-26(28)29-21-30-27(25)32/h21-22,24,33H,2-20,23H2,1H3,(H,34,35)(H2,28,29,30)/t24-/m0/s1

Standard InChI Key:  GYFARMYRBNCELX-DEOSSOPVSA-N

Alternative Forms

1. Parent:

   

   ALA1774183

   [(1S)-1-[(6-aminopurin-9-yl)methyl]-2-hydroxy-ethoxy]methyl-(2-hexadecoxyethoxy)phosphinic 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: 571.70

Molecular Weight (Monoisotopic): 571.3499

AlogP: 5.44

#Rotatable Bonds: 25

Polar Surface Area: 154.84

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.88

CX Basic pKa: 4.72

CX LogP: 1.99

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.10

Np Likeness Score: 0.07

References

1. Ruiz J, Beadle JR, Buller RM, Schreiwer J, Prichard MN, Keith KA, Lewis KC, Hostetler KY..  (2011)  Synthesis, metabolic stability and antiviral evaluation of various alkoxyalkyl esters of cidofovir and 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine.,  19  (9): [PMID:21493074] [10.1016/j.bmc.2011.03.034]

Source

Source(1):

• Scientific Literature