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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2020-02-26 21:39:27 UTC |
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HMDB ID | HMDB0014340 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Vidarabine |
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Description | Vidarabine, also known as ara a or spongoadenosine, 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. Vidarabine is a synthetic purine nucleoside analogue with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). By acting as a substrate for viral DNA polymerase, ara-ATP competitively inhibits dATP leading to the formation of ‘faulty’ DNA. Vidarabine is a drug which is used for treatment of chickenpox - varicella, herpes zoster and herpes simplex. The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. Vidarabine is a strong basic compound (based on its pKa). A nucleoside antibiotic isolated from Streptomyces antibioticus. No untoward effects should result from ingestion of the entire contents of the tube. |
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Structure | |
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Synonyms | Value | Source |
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2-(6-AMINO-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol | ChEBI | 9-beta-D-Arabinofuranosyl-9H-purin-6-amine | ChEBI | 9-beta-D-Arabinofuranosyladenine | ChEBI | Spongoadenosine | ChEBI | Vidarabine anhydrous | Kegg | ARA-a | Kegg | Armes | Kegg | 9-b-D-Arabinofuranosyl-9H-purin-6-amine | Generator | 9-Β-D-arabinofuranosyl-9H-purin-6-amine | Generator | 9-b-D-Arabinofuranosyladenine | Generator | 9-Β-D-arabinofuranosyladenine | Generator | 9-beta-D-Arabinofuranosyl-adenine | HMDB | Adenine arabinoside | HMDB | Ara-ATP | HMDB | Araadenosine | HMDB | Arabinoside adenine | HMDB | Arabinosyl adenine | HMDB | Arabinosyladenine | HMDB | a, alpha-Ara | HMDB | Ara a | HMDB | Arabinofuranosyladenine | HMDB | Monarch brand OF vidarabine | HMDB | ViraA | HMDB | alpha Ara a | HMDB | alpha D Arabinofuranosyladenine | HMDB | alpha-Ara a | HMDB | 9 beta Arabinofuranosyladenine | HMDB | 9 beta D Arabinofuranosyladenine | HMDB | a, Ara | HMDB | beta Ara a | HMDB | Arabinoside, adenine | HMDB | alpha-D-Arabinofuranosyladenine | HMDB | 9-beta-Arabinofuranosyladenine | HMDB | a, beta-Ara | HMDB | Parke davis brand OF vidarabine | HMDB | Vira a | HMDB | Vira-a | HMDB | beta-Ara a | HMDB | Vidarabine | ChEBI |
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Chemical Formula | C10H13N5O4 |
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Average Molecular Weight | 267.2413 |
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Monoisotopic Molecular Weight | 267.096753929 |
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IUPAC Name | (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
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Traditional Name | armes |
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CAS Registry Number | 24356-66-9 |
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SMILES | NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1 |
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InChI Key | OIRDTQYFTABQOQ-UHTZMRCNSA-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-aminopurine
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monosaccharide
- N-substituted imidazole
- Pyrimidine
- Imidolactam
- Tetrahydrofuran
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organic oxygen compound
- Organic nitrogen compound
- Alcohol
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organooxygen compound
- Amine
- Primary alcohol
- Primary amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 14 g/L | Not Available | LogP | -2.115 | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4l-9350000000-ed8639e5b54e46825628 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-014i-1492400000-1fe7f0d7ca11fdb4800f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-000i-2910000000-e18a8d00eb0e73aa6dec | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-000i-2910000000-e18a8d00eb0e73aa6dec | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0940000000-42bee9785f9b55b32eea | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-c8cda6a661ace060572c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-2900000000-0304a85c3951aa1cb41a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0159-0690000000-0258e5851611884483d9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-e6b8fc6980387f646d64 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053r-2900000000-1e0cad8d044715d90f12 | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00194 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00194 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00194 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 20400 |
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KEGG Compound ID | C07195 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Vidarabine |
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METLIN ID | Not Available |
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PubChem Compound | 21704 |
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PDB ID | RAB |
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ChEBI ID | 45327 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Feher Z, Mishra NC: An aphidicolin-resistant mutant of Chinese hamster ovary cell with altered DNA polymerase and 3' exonuclease activities. Biochim Biophys Acta. 1995 Aug 22;1263(2):141-6. [PubMed:7640304 ]
- Russell RR 3rd, Bergeron R, Shulman GI, Young LH: Translocation of myocardial GLUT-4 and increased glucose uptake through activation of AMPK by AICAR. Am J Physiol. 1999 Aug;277(2 Pt 2):H643-9. [PubMed:10444490 ]
- Moore CL, Chiaramonte M, Higgins T, Kuchta RD: Synthesis of nucleotide analogues that potently and selectively inhibit human DNA primase. Biochemistry. 2002 Nov 26;41(47):14066-75. [PubMed:12437364 ]
- Kuchta RD, Ilsley D, Kravig KD, Schubert S, Harris B: Inhibition of DNA primase and polymerase alpha by arabinofuranosylnucleoside triphosphates and related compounds. Biochemistry. 1992 May 19;31(19):4720-8. [PubMed:1581321 ]
- Chen J, Hudson E, Chi MM, Chang AS, Moley KH, Hardie DG, Downs SM: AMPK regulation of mouse oocyte meiotic resumption in vitro. Dev Biol. 2006 Mar 15;291(2):227-38. Epub 2006 Jan 26. [PubMed:16443210 ]
- Thompson HC, Kuchta RD: Arabinofuranosyl nucleotides are not chain-terminators during initiation of new strands of DNA by DNA polymerase alpha-primase. Biochemistry. 1995 Sep 5;34(35):11198-203. [PubMed:7545435 ]
- Feher Z, Mishra NC: Aphidicolin-resistant Chinese hamster ovary cells possess altered DNA polymerases of the alpha-family. Biochim Biophys Acta. 1994 May 17;1218(1):35-47. [PubMed:7514891 ]
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