| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-26 05:48:38 UTC |
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| Update Date | 2016-11-09 01:21:19 UTC |
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| Accession Number | CHEM035487 |
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| Identification |
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| Common Name | Arabinosylhypoxanthine |
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| Class | Small Molecule |
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| Description | Arabinosylhypoxanthine is found to have a potent antiviral activity for herpes simplex infected cells. The final metabolite in the conversion of Arabinosyladenine-5'-monophosphate to arabinosyladenine then to Arabinosylhypoxanthine. |
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| Contaminant Sources | |
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Ara-HX | HMDB, MeSH | | 9 beta-D-Arabinofuranosyl-1,9-dihydro-6H-purin-6-one | MeSH, HMDB | | Hypoxanthine arabinoside | MeSH, HMDB | | 9 beta-D-Arabinofuranosylhypoxanthine | MeSH, HMDB | | AraHx | MeSH, HMDB | | Ara-H | MeSH, HMDB |
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| Chemical Formula | C10H12N4O5 |
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| Average Molecular Mass | 268.226 g/mol |
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| Monoisotopic Mass | 268.081 g/mol |
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| CAS Registry Number | 7013-16-3 |
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| IUPAC Name | 9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one |
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| Traditional Name | 9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one |
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| SMILES | OC[C@H]1OC([C@@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O |
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| InChI Identifier | InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7+,10?/m1/s1 |
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| InChI Key | UGQMRVRMYYASKQ-KBNQYOMWSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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| Class | Purine nucleosides |
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| Sub Class | Not Available |
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| Direct Parent | Purine nucleosides |
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| Alternative Parents | |
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| Substituents | - Purine nucleoside
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Pentose monosaccharide
- Purinone
- Imidazopyrimidine
- Purine
- Pyrimidone
- Pyrimidine
- Monosaccharide
- N-substituted imidazole
- Vinylogous amide
- Tetrahydrofuran
- Heteroaromatic compound
- Azole
- Imidazole
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Alcohol
- Organonitrogen compound
- Organic nitrogen compound
- Organooxygen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adl-9250000000-d6ee10ae0804bda3e4ce | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0gc0-3392100000-105fd86588f87bbc7682 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0940000000-1edfa7642cf5a4fed66d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-c4a771b28fab50986335 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06ri-1900000000-bad238ac23d41426077a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014r-0590000000-987a2099b121adf31362 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-1f1240b42ef89dc97aae | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4u-3900000000-ffc6c0f2b3a8bd03b941 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0910000000-33dc079e70e0b33bf986 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-b2e36fb98660834d7d24 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-2747044cf1ae427677f9 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014s-0490000000-6a0e0735ea6ec840b8a6 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-1900000000-1e57f5864e9a304e81c6 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4r-2900000000-a2ec1536ad3b3b6df400 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0003040 |
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| FooDB ID | FDB023100 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | 3022 |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 24654354 |
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| ChEBI ID | 705435 |
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| PubChem Compound ID | 46874582 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. Reist, Elmer J.; Benitez, Allen; Goodman, Leon; Baker, B. R.; Lee, William W. Potential anticancer agents. LXXVI. Synthesis of purine nucleosides of b-D-arabinofuranose. Journal of Organic Chemistry (1962), 27 3274-9. | | 2. Schwartz PM, Shipman C Jr, Drach JC: Antiviral activity of arabinosyladenine and arabinosylhypoxanthine in herpes simplex virus-infected KB cells: selective inhibition of viral deoxyribonucleic acid synthesis in the presence of an adenosine deaminase inhibitor. Antimicrob Agents Chemother. 1976 Jul;10(1):64-74. | | 3. Buchanan RA, Kinkel AW, Alford CA Jr, Whitley RJ: Plasma levels and urinary excretion of vidarabine after repeated dosing. Clin Pharmacol Ther. 1980 May;27(5):690-6. | | 4. Chang T, Glazko AJ: Effect of an adenosine deaminase inhibitor on the uptake and metabolism of arabinosyl adenine (Vidarabine) by intact human erythrocytes. Res Commun Chem Pathol Pharmacol. 1976 May;14(1):127-40. | | 5. McCann WP, Hall LM, Siler W, Barton N, Whitley RJ: High-pressure liquid chromatographic methods for determining arabinosyladenine-5'-monophosphate, arabinosyladenine, and arabinosylhypoxanthine in plasma and urine. Antimicrob Agents Chemother. 1985 Aug;28(2):265-73. |
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