3-(15-methylhexadecyloxy)propyl hydrogen((S)-1-(6-amino-9H-purin-9-yl)-3-hydroxypropan-2-yloxy)methylphosphonate

ID: ALA1652472

Chembl Id: CHEMBL1652472

PubChem CID: 16066674

Max Phase: Preclinical

Molecular Formula: C29H54N5O6P

Molecular Weight: 599.75

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H54N5O6P/c1-25(2)16-13-11-9-7-5-3-4-6-8-10-12-14-17-38-18-15-19-40-41(36,37)24-39-26(21-35)20-34-23-33-27-28(30)31-22-32-29(27)34/h22-23,25-26,35H,3-21,24H2,1-2H3,(H,36,37)(H2,30,31,32)/t26-/m0/s1

Standard InChI Key:  AFYBRMBNNNXCLD-SANMLTNESA-N

Alternative Forms

1. Parent:

   

   ALA1652472

   [(1S)-1-[(6-aminopurin-9-yl)methyl]-2-hydroxy-ethoxy]methyl-[3-(15-methylhexadecoxy)propoxy]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: 599.75

Molecular Weight (Monoisotopic): 599.3812

AlogP: 6.08

#Rotatable Bonds: 26

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: 1.40

CX Basic pKa: 4.72

CX LogP: 2.67

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.09

Np Likeness Score: 0.18

References

1. Morrey JD, Korba BE, Beadle JR, Wyles DL, Hostetler KY..  (2009)  Alkoxyalkyl esters of 9-(s)-(3-hydroxy-2-phosphonomethoxypropyl) adenine are potent and selective inhibitors of hepatitis B virus (HBV) replication in vitro and in HBV transgenic mice in vivo.,  53  (7): [PMID:19398648] [10.1128/aac.00114-09]

2. 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