Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:37:51 UTC |
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Updated at | 2020-11-18 16:38:42 UTC |
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CannabisDB ID | CDB004798 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Deoxyguanosine |
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Description | Deoxyguanosine, also known as dG, 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. Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. Deoxyguanosine is an extremely weak basic (essentially neutral) compound (based on its pKa). Deoxyguanosine exists in all living species, ranging from bacteria to humans. Within humans, deoxyguanosine participates in a number of enzymatic reactions. In particular, deoxyguanosine can be biosynthesized from 2'-deoxyguanosine 5'-monophosphate; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In addition, deoxyguanosine can be converted into 2'-deoxyguanosine 5'-monophosphate; which is mediated by the enzyme deoxyguanosine kinase. In humans, deoxyguanosine is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. It is like guanosine, but with one oxygen atom removed. 8-OHDeoxyguanosine is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. It is a nucleoside component of DNA. Deoxyguanosine 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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2-Amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-9H-purin-6-ol | ChEBI | 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-guanine | ChEBI | dG | ChEBI | Guanine deoxy nucleoside | ChEBI | 2'-Deoxyguanosine | Kegg | 2-Amino-9-(2-deoxy-9-b-D-ribofuranosyl)-9H-purin-6-ol | Generator | 2-Amino-9-(2-deoxy-9-β-D-ribofuranosyl)-9H-purin-6-ol | Generator | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-guanine | Generator | 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine | Generator | 2'-Deoxy-guanosine | HMDB | 2-Deoxyguanosine | HMDB | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine | HMDB | 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-guanine | HMDB | 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine | HMDB | Desoxyguanosine | HMDB | Guanine deoxyriboside | HMDB | Deoxyguanosine | ChEBI |
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Chemical Formula | C10H13N5O4 |
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Average Molecular Weight | 267.24 |
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Monoisotopic Molecular Weight | 267.0968 |
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IUPAC Name | 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one |
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Traditional Name | 2-deoxyguanosine |
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CAS Registry Number | 961-07-9 |
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SMILES | NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1 |
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InChI Identifier | InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1 |
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InChI Key | YKBGVTZYEHREMT-KVQBGUIXSA-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-oxopurine
- Hypoxanthine
- Purinone
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Pyrimidone
- N-substituted imidazole
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Vinylogous amide
- Tetrahydrofuran
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Amine
- Primary amine
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organopnictogen compound
- 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 | Route of exposure: Source: Biological location: |
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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 | 300 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | -1.30 | BALZARINI,JM ET AL. (1989) |
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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 | Deoxyguanosine, non-derivatized, GC-MS Spectrum | splash10-001j-0891000000-3d776d25cb03b01b9339 | Spectrum | GC-MS | Deoxyguanosine, 4 TMS, GC-MS Spectrum | splash10-0f8a-2960000000-dfb317b7b1eb025d909e | Spectrum | GC-MS | Deoxyguanosine, 5 TMS, GC-MS Spectrum | splash10-0udi-2913000000-1b2f5de9c93a151947ec | Spectrum | GC-MS | Deoxyguanosine, non-derivatized, GC-MS Spectrum | splash10-001j-0891000000-3d776d25cb03b01b9339 | Spectrum | GC-MS | Deoxyguanosine, non-derivatized, GC-MS Spectrum | splash10-0f8a-2960000000-dfb317b7b1eb025d909e | Spectrum | GC-MS | Deoxyguanosine, non-derivatized, GC-MS Spectrum | splash10-0udi-2913000000-1b2f5de9c93a151947ec | Spectrum | Predicted GC-MS | Deoxyguanosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052p-9580000000-831d1b4a56d55342e5d9 | Spectrum | Predicted GC-MS | Deoxyguanosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-8009000000-43fe5e369133cc5b35c0 | Spectrum | Predicted GC-MS | Deoxyguanosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Deoxyguanosine, TBDMS_2_2, 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 - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0900000000-1ff2faf768c32875ae94 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0900000000-6ecd3556539c87465829 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0f89-2900000000-3c7a46a8b1ebc3478b0e | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0090000000-d7b5f1fd49de4c188c2b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-066r-1290000000-f1789943f3a3aa93bf11 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0pb9-1960000000-cae86b9369b467a619ac | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-2930000000-59733590e9e1f1f9e3ab | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a59-3900000000-63f2d871818a0f9ea2c4 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0udi-0490000000-a0d35f9580527e157997 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0udi-0940000000-501ccdb19ac1399ea47d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0pb9-2900000000-3c8141b790d1e751030c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0k96-6900000000-218b8cf773fa785dd6fc | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0006-9700000000-16fac3cb96899ba7c58c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-0udi-0900000000-c020044f3d53ad944e38 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-0udi-0900000000-09d1a1821d4e622a1f9a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0090000000-d7b5f1fd49de4c188c2b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-066r-1290000000-cf5beb73c1ce61ceb87b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0pb9-1960000000-cae86b9369b467a619ac | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-2930000000-08d635c63c26f8baa811 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0920000000-d7d80ec246617036e55e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-c5bd180b555397bc1ae5 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0900000000-c54d0a1dec8712b2b8f7 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0290000000-393ce4bbd1a38882e581 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0910000000-7bc10bc144a1a343b08f | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pbc-4900000000-c3082fcc9288ad93f897 | Spectrum |
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NMR | |
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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 | Not Available |
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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 | HMDB0000085 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB012064 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 163230 |
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KEGG Compound ID | C00330 |
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BioCyc ID | DEOXYGUANOSINE |
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BiGG ID | 34637 |
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Wikipedia Link | Deoxyguanosine |
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METLIN ID | 3395 |
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PubChem Compound | 187790 |
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PDB ID | Not Available |
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ChEBI ID | 17172 |
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References |
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General References | Not Available |
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