Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:38:10 UTC |
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Updated at | 2020-12-07 19:10:58 UTC |
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CannabisDB ID | CDB004801 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Deoxyadenosine |
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Description | Deoxyadenosine, also known as dA, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. Deoxyadenosine is a strong basic compound (based on its pKa). Deoxyadenosine exists in all living species, ranging from bacteria to humans. Within humans, deoxyadenosine participates in a number of enzymatic reactions. In particular, deoxyadenosine can be converted into adenine and deoxyribose 1-phosphate through its interaction with the enzyme purine nucleoside phosphorylase. In addition, deoxyadenosine can be converted into deoxyinosine through its interaction with the enzyme adenosine deaminase. A purine 2'-deoxyribonucleoside having adenine as the nucleobase. In humans, deoxyadenosine is involved in mercaptopurine action pathway. Outside of the human body, Deoxyadenosine is found, on average, in the highest concentration within beers. Deoxyadenosine has also been detected, but not quantified in, milk (cow). This could make deoxyadenosine a potential biomarker for the consumption of these foods. Deoxyadenosine is a potentially toxic compound. Deoxyadenosine, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and eosinophilic esophagitis; deoxyadenosine has also been linked to several inborn metabolic disorders including adenosine deaminase deficiency and adenylosuccinate lyase deficiency. Deoxyadenosine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol | ChEBI | 5-(6-AMINO-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol | ChEBI | 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine | ChEBI | 9-(2-Deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine | ChEBI | Adenine deoxyribonucleoside | ChEBI | Adenyldeoxyriboside | ChEBI | dA | ChEBI | 2'-Deoxyadenosine | Kegg | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine | Generator | 9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine | Generator | 9-(2-Deoxy-b-D-ribofuranosyl)-9H-purin-6-amine | Generator | 9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine | Generator | 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-ribofuranose | HMDB | 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-ribofuranose | HMDB | 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose | HMDB | 2-Deoxyadenosine | HMDB | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-amine | HMDB | 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-amine | HMDB | 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-9H-purin-6-amine | HMDB | 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine | HMDB | 9-(2-Deoxy-beta-delta-ribofuranosyl)-9H-purin-6-amine | HMDB | Adenine deoxyribose | HMDB | Adenine-9 2-deoxy-b-D-erythro-pentofuranoside | HMDB | Adenine-9 2-deoxy-beta-D-erythro-pentofuranoside | HMDB | Adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside | HMDB | Desoxyadenosine | HMDB | Deoxyadenosine | ChEBI |
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Chemical Formula | C10H13N5O3 |
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Average Molecular Weight | 251.24 |
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Monoisotopic Molecular Weight | 251.1018 |
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IUPAC Name | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol |
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Traditional Name | 2-deoxyadenosine |
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CAS Registry Number | 958-09-8 |
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SMILES | NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC=N1 |
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InChI Identifier | InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1 |
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InChI Key | OLXZPDWKRNYJJZ-RRKCRQDMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. |
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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 | Purine 2'-deoxyribonucleosides |
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Direct Parent | Purine 2'-deoxyribonucleosides |
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Alternative Parents | |
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Substituents | - Purine 2'-deoxyribonucleoside
- 6-aminopurine
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- N-substituted imidazole
- Pyrimidine
- Imidolactam
- Azole
- Imidazole
- Heteroaromatic compound
- Tetrahydrofuran
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Amine
- Primary amine
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Alcohol
- Organic nitrogen compound
- Organic oxygen compound
- 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 | Source: Biological location: |
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Role | Indirect biological role: |
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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 | 189 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | -0.55 | HANSCH,C ET AL. (1995) |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Deoxyadenosine, 3 TMS, GC-MS Spectrum | splash10-0pbc-1950000000-892b755b10f34bcfa1c7 | Spectrum | GC-MS | Deoxyadenosine, 3 TMS, GC-MS Spectrum | splash10-05fr-9750000000-34ebf7e59598c6551f52 | Spectrum | GC-MS | Deoxyadenosine, 3 TMS, GC-MS Spectrum | splash10-0pbc-2950000000-9d52e7dcd83de5a30aef | Spectrum | GC-MS | Deoxyadenosine, non-derivatized, GC-MS Spectrum | splash10-0pbc-1950000000-892b755b10f34bcfa1c7 | Spectrum | GC-MS | Deoxyadenosine, non-derivatized, GC-MS Spectrum | splash10-05fr-9750000000-34ebf7e59598c6551f52 | Spectrum | GC-MS | Deoxyadenosine, non-derivatized, GC-MS Spectrum | splash10-0pbc-2950000000-9d52e7dcd83de5a30aef | Spectrum | Predicted GC-MS | Deoxyadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000x-9550000000-219c39ab05ecbebb53ee | Spectrum | Predicted GC-MS | Deoxyadenosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ge9-6917000000-51808985bdc9abeb3cb3 | Spectrum | Predicted GC-MS | Deoxyadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyadenosine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0udr-1790000000-c0d4c0cc085cab7c2dcf | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-000i-1900000000-e2abd19062db64ff67be | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-000i-2900000000-1b8d5c847c2b1955056e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-000i-5900000000-845c20e0f6bd5494b6dc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-004r-8900000000-484d9f08e4e28fab1f70 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-000i-0900000000-e852451e7253e0de72be | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0390000000-fba17d1430b371138db2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-000i-0930000000-931c7b084c33f9122af4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0900000000-66ae7ac8bd510a173402 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0900000000-c71d67857e2136dc7666 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0udr-1790000000-cfbdf2e3950e7987b94b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-1900000000-a3c367588a28d36cf5f0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-2900000000-1b8d5c847c2b1955056e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-5900000000-f950493ce420caae6a66 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004r-8900000000-61ed5b4b3e748a449803 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-000i-0900000000-31d03c242f14d91a718c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0390000000-fba17d1430b371138db2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0930000000-931c7b084c33f9122af4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000i-0900000000-81ac782a59b2ca52f52b | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0920000000-2e897a458cf4c7af381c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-f52b5322fde2e3722903 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-fcb0a5032b8607fd8b11 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0290000000-bec96a9658c683fa0d9b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0910000000-b504aa725d20d6213b20 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053r-2900000000-d09551db93d558a5aed7 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Purine Metabolism | | | Adenosine Deaminase Deficiency | | Not Available | Adenylosuccinate Lyase Deficiency | | Not Available | Gout or Kelley-Seegmiller Syndrome | | Not Available | Lesch-Nyhan Syndrome (LNS) | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | Not Available |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000101 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB021894 |
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KNApSAcK ID | C00019281 |
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Chemspider ID | 13135 |
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KEGG Compound ID | C00559 |
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BioCyc ID | DEOXYADENOSINE |
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BiGG ID | 35352 |
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Wikipedia Link | Deoxyadenosine |
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METLIN ID | 3382 |
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PubChem Compound | 13730 |
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PDB ID | Not Available |
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ChEBI ID | 17256 |
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References |
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General References | Not Available |
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