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113892-17-4 | 9H-Purin-6-amine, 9-[[(5S)-2-hydroxy-2-oxido-1,4,2-dioxaphosphorinan-5-yl]methyl]-
CAS No: 113892-17-4 Catalog No: AG000A0E MDL No:
Product Description
Catalog Number:
AG000A0E
Chemical Name:
9H-Purin-6-amine, 9-[[(5S)-2-hydroxy-2-oxido-1,4,2-dioxaphosphorinan-5-yl]methyl]-
CAS Number:
113892-17-4
Molecular Formula:
C9H12N5O4P
Molecular Weight:
285.1964
IUPAC Name:
9-[[(5S)-2-hydroxy-2-oxo-1,4,2λ5-dioxaphosphinan-5-yl]methyl]purin-6-amine
InChI:
InChI=1S/C9H12N5O4P/c10-8-7-9(12-3-11-8)14(4-13-7)1-6-2-18-19(15,16)5-17-6/h3-4,6H,1-2,5H2,(H,15,16)(H2,10,11,12)/t6-/m0/s1
InChI Key:
LNUMZUZGQXHRIL-LURJTMIESA-N
SMILES:
Nc1ncnc2c1ncn2C[C@H]1COP(=O)(CO1)O
Properties
Complexity:
386
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
285.063g/mol
Formal Charge:
0
Heavy Atom Count:
19
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
285.2g/mol
Monoisotopic Mass:
285.063g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
125A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.7
Literature
| Title | Journal |
|---|---|
| Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies. | Journal of medicinal chemistry 20110825 |
| Intraocular properties of an alkoxyalkyl derivative of cyclic 9-(S)-(3-hydroxyl-2-phosphonomehoxypropyl) adenine, an intravitreally injectable anti-HCMV drug in rabbit and guinea pig. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20071001 |
| A new approach to the synthesis of optically active alkylated adenine derivatives. | Bioorganic & medicinal chemistry letters 20040621 |
| Antivaccinia activities of acyclic nucleoside phosphonate derivatives in epithelial cells and organotypic cultures. | Antimicrobial agents and chemotherapy 20021101 |
| Cidofovir in the treatment of poxvirus infections. | Antiviral research 20020701 |
| Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6. | Antiviral research 19951201 |
| Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus. | European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 19950401 |
| Antiviral activity of anti-cytomegalovirus agents (HPMPC, HPMPA) assessed by a flow cytometric method and DNA hybridization technique. | Antiviral research 19910701 |
| (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication. | Antimicrobial agents and chemotherapy 19881201 |
| Antiviral activity of phosphonylmethoxyalkyl derivatives of purine and pyrimidines. | Antiviral research 19871201 |
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