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

ID: ALA487297

Chembl Id: CHEMBL487297

PubChem CID: 10031478

Max Phase: Preclinical

Molecular Formula: C29H54N5O6P

Molecular Weight: 599.75

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H54N5O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-38-19-20-40-41(36,37)25-39-26(22-35)21-34-24-33-27-28(30)31-23-32-29(27)34/h23-24,26,35H,2-22,25H2,1H3,(H,36,37)(H2,30,31,32)/t26-/m0/s1

Standard InChI Key:  HMMRNEAGFOALKT-SANMLTNESA-N

Alternative Forms

1. Alternative Forms:

   

   ALA487297

   sodium;[(2S)-1-(6-aminopurin-9-yl)-3-hydroxypropan-2-yl]oxymethyl-(2-octadecoxyethoxy)phosphinate

2. Parent:

   

   ALA487297

   [(1S)-1-[(6-Aminopurin-9-yl)methyl]-2-hydroxy-ethoxy]methyl-(2-octadecoxyethoxy)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: 6.22

#Rotatable Bonds: 27

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: 2.83

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.08

Np Likeness Score: 0.07

References

1. Quenelle DC, Collins DJ, Herrod BP, Keith KA, Trahan J, Beadle JR, Hostetler KY, Kern ER..  (2007)  Effect of oral treatment with hexadecyloxypropyl-[(S)-9-(3-hydroxy-2- phosphonylmethoxypropyl)adenine] [(S)-HPMPA] or octadecyloxyethyl-(S)-HPMPA on cowpox or vaccinia virus infections in mice.,  51  (11): [PMID:17846137] [10.1128/aac.00184-07]

2. Randhawa P, Zemlicka J, Sauerbrei A, Meier C, Hostetler KY, Beadle JR, Farasati NA, Huang Y, Bradley M..  (2008)  Anti-BK virus activity of nucleoside analogs.,  52  (4): [PMID:18285481] [10.1128/aac.01241-07]

3. Botros SS, William S, Beadle JR, Valiaeva N, Hostetler KY..  (2009)  Antischistosomal activity of hexadecyloxypropyl cyclic 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine and other alkoxyalkyl esters of acyclic nucleoside phosphonates assessed by schistosome worm killing in vitro.,  53  (12): [PMID:19704122] [10.1128/aac.00840-09]

4. Wyles DL, Kaihara KA, Korba BE, Schooley RT, Beadle JR, Hostetler KY..  (2009)  The octadecyloxyethyl ester of (S)-9-[3-hydroxy-2-(phosphonomethoxy) propyl]adenine is a potent and selective inhibitor of hepatitis C virus replication in genotype 1A, 1B, and 2A replicons.,  53  (6): [PMID:19289518] [10.1128/aac.01546-08]

5. 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]

Source

Source(1):

• Scientific Literature