| Identification | Back Directory | [Name]
9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine | [CAS]
92999-29-6 | [Synonyms]
GS 0577
(S)-HPMPA
(S)-9-(3-Hydroxy-2-phosphonomethoxypropyl)adenine
(S)-9-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine
9-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]adenine
9-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]-9H-purine-6-amine
[[(S)-2-(6-Amino-9H-purin-9-yl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid
(S)-(((1-(6-Amino-9H-purin-9-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonic acid
[[(1S)-1-(Hydroxymethyl)-2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid
Phosphonic acid, P-[[(1S)-2-(6-amino-9H-purin-9-yl)-1-(hydroxymethyl)ethoxy]methyl]- | [Molecular Formula]
C9H14N5O5P | [MOL File]
92999-29-6.mol | [Molecular Weight]
303.21 |
| Chemical Properties | Back Directory | [Melting point ]
255-257 °C | [Boiling point ]
719.6±70.0 °C(Predicted) | [density ]
1.91±0.1 g/cm3(Predicted) | [pka]
2.31±0.10(Predicted) | [InChI]
InChI=1S/C9H14N5O5P/c10-8-7-9(12-3-11-8)14(4-13-7)1-6(2-15)19-5-20(16,17)18/h3-4,6,15H,1-2,5H2,(H2,10,11,12)(H2,16,17,18)/t6-/m0/s1 | [InChIKey]
FRPXSOOHWNMLPH-LURJTMIESA-N | [SMILES]
P(CO[C@H](CO)CN1C2C(N=C1)=C(N)N=CN=2)(=O)(O)O |
| Hazard Information | Back Directory | [Description]
9-((S)-3-Hydroxy-2-(phosphonomethoxy)propyl)adenine [(S)-HPMPA] is a non-cyclic nucleotide analogue that acts as a potent and selective inhibitor of African swine fever virus (ASFV) replication. It has been reported that (S)-HPMPA exerts a specific, dose-dependent inhibitory effect on viral DNA synthesis. Furthermore, (S)-HPMPA also inhibits the production of late viral proteins (particularly IP-73) in ASFV-infected MS and Vero cells[1]. | [Preparation]
9-(S)-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA) was prepared from 9-(S)-(2,3-dihydroxypropyl)adenine (DHPA) via its 3-O-chloromethanephosphonate[2]. | [References]
[1] O. Arzuza . (1988). Inhibition of African swine fever virus DNA synthesis by (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine. Biochemical and Biophysical Research Communications, 154 1, Pages 27-32. https://doi.org/10.1016/0006-291X(88)90644-4
[2] A Holý, I R. (1987). Stereospecific syntheses of 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA). Nucleic Acids Symposium Series, 18, 33–36.
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