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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:18:58 UTC |
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Update Date | 2020-06-04 20:45:19 UTC |
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BMDB ID | BMDB0000050 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Adenosine |
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Description | Adenosine, also known as adenocard or ade-rib, 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. Adenosine is a drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Adenosine exists in all living species, ranging from bacteria to humans. Adenosine is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol | ChEBI | 6-Amino-9-beta-D-ribofuranosyl-9H-purine | ChEBI | 9-beta-D-Ribofuranosidoadenine | ChEBI | 9-beta-D-Ribofuranosyl-9H-purin-6-amine | ChEBI | Ade-rib | ChEBI | Adenine deoxyribonucleoside | ChEBI | Adenocard | ChEBI | Adenocor | ChEBI | Adenoscan | ChEBI | Adenosin | ChEBI | Adenyldeoxyriboside | ChEBI | Ado | ChEBI | beta-D-Adenosine | ChEBI | Deoxyadenosine | ChEBI | Desoxyadenosine | ChEBI | 6-Amino-9-b-D-ribofuranosyl-9H-purine | Generator | 6-Amino-9-β-D-ribofuranosyl-9H-purine | Generator | 9-b-D-Ribofuranosidoadenine | Generator | 9-Β-D-ribofuranosidoadenine | Generator | 9-b-D-Ribofuranosyl-9H-purin-6-amine | Generator | 9-Β-D-ribofuranosyl-9H-purin-6-amine | Generator | b-D-Adenosine | Generator | Β-D-adenosine | Generator | 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-ribofuranose | HMDB | 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-ribofuranose | HMDB | 6-Amino-9beta-D-ribofuranosyl-9H-purine | HMDB | 6-Amino-9beta-delta-ribofuranosyl-9H-purine | HMDB | 9-beta-D-Arabinofuranosyladenine | HMDB | 9-beta-D-Ribofuranosyladenine | HMDB | 9-beta-delta-Arabinofuranosyladenine | HMDB | 9-beta-delta-Ribofuranosidoadenine | HMDB | 9-beta-delta-Ribofuranosyl-9H-purin-6-amine | HMDB | 9-beta-delta-Ribofuranosyladenine | HMDB | 9beta-D-Ribofuranosyl-9H-purin-6-amine | HMDB | 9beta-D-Ribofuranosyladenine | HMDB | 9beta-delta-Ribofuranosyl-9H-purin-6-amine | HMDB | 9beta-delta-Ribofuranosyladenine | HMDB | Adenine nucleoside | HMDB | Adenine riboside | HMDB | Adenine-9beta-D-ribofuranoside | HMDB | Adenine-9beta-delta-ribofuranoside | HMDB | beta-Adenosine | HMDB | beta-delta-Adenosine | HMDB | Boniton | HMDB | Myocol | HMDB | Nucleocardyl | HMDB | Sandesin | HMDB |
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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 | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 58-61-7 |
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SMILES | Not Available |
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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-KQYNXXCUSA-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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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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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 | 235.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 37 mg/mL | Human Metabolome Project | LogP | -1.05 | HANSCH,C ET AL. (1995) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - All Tissues
- Colostrum
- Liver
- Mammary Gland
- Milk
- Muscle
- Placenta
- Testis
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Pathways | |
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Normal Concentrations |
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All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1.4 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 150 +/- 114 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000050 |
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DrugBank ID | DB00640 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003554 |
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KNApSAcK ID | C00007444 |
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Chemspider ID | 54923 |
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KEGG Compound ID | C00212 |
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BioCyc ID | ADENOSINE |
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BiGG ID | 34273 |
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Wikipedia Link | Adenosine |
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METLIN ID | 86 |
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PubChem Compound | 60961 |
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PDB ID | Not Available |
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ChEBI ID | 16335 |
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References |
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Synthesis Reference | Liao, Ben-ren; Yuan, Zhen-wen. Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
- Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. [PubMed:11242448 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
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