9-S-[3-hydroxy-2-(Phosphonomethoxy)propyl]-adenine

ID: ALA472584

Chembl Id: CHEMBL472584

PubChem CID: 6479185

Max Phase: Preclinical

Molecular Formula: C28H52N5O6P

Molecular Weight: 585.73

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H52N5O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-37-18-16-19-39-40(35,36)24-38-25(21-34)20-33-23-32-26-27(29)30-22-31-28(26)33/h22-23,25,34H,2-21,24H2,1H3,(H,35,36)(H2,29,30,31)/t25-/m0/s1

Standard InChI Key:  DPIOHFGAQQGXIS-VWLOTQADSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA472584

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

2. Parent:

   

   ALA472584

   [(1S)-1-[(6-aminopurin-9-yl)methyl]-2-hydroxy-ethoxy]methyl-(3-hexadecoxypropoxy)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: 585.73

Molecular Weight (Monoisotopic): 585.3655

AlogP: 5.83

#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: 2.37

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.09

Np Likeness Score: 0.11

References

1. Painter GR, Almond MR, Trost LC, Lampert BM, Neyts J, De Clercq E, Korba BE, Aldern KA, Beadle JR, Hostetler KY..  (2007)  Evaluation of hexadecyloxypropyl-9-R-[2-(Phosphonomethoxy)propyl]- adenine, CMX157, as a potential treatment for human immunodeficiency virus type 1 and hepatitis B virus infections.,  51  (10): [PMID:17646420] [10.1128/aac.00460-07]

2. 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]

3. 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]

4. 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]

5. 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]

6. 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]

7. 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